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DOI: 10.1055/s-0029-1218699
Cinchona Alkaloids in Asymmetric Organocatalysis
Publikationsverlauf
Publikationsdatum:
12. März 2010 (online)
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Abstract
This article reviews the applications of cinchona alkaloids as asymmetric catalysts. In the last few years, characterized by the resurgence of interest in asymmetric organocatalysis, cinchona derivatives have been shown to catalyze an outstanding array of chemical reactions, often with remarkable stereoselectivity. This work presents an overview of the transformations developed in the period from 2001 through 2009, highlighting applications in the synthesis of bioactive molecules and natural products.
1 Introduction
2 Additions to Carbonyls
3 Additions to Imines
4 Conjugate Additions
5 Additions to Olefins
6 Nucleophilic Substitutions
7 Electrophilic Halogenations
8 Opening of Cyclic Anhydrides
9 Acylations
10 Cycloadditions
11 Rearrangements
12 Decarboxylations
13 Miscellaneous
14 Conclusions and Outlook
List of abbreviations: Alloc, allyloxycarbonyl; Boc, tert-butyloxycarbonyl; Bs, benzenesulfonyl; BTTP, tert-butyliminotri(pyrrolidino)phosphorane; Cbz, benzyloxycarbonyl; DABCO, 1,4-diazabicyclo[2.2.2]octane; DBAD, dibenzyl azodicarboxylate; DBU, 1,8-diazabicycloundec-7-ene; DCE, 1,2-dichloroethane; DFT, density functional theory; DIPEA, N,N-diisopropylethylamine; DNP, 2,4-dinitrophenyl; DMB, 3,4-dimethoxybenzoyl; DPM, diphenylmethyl; DTAD, di-tert-butyl azodicarboxylate; EVE, ethyl vinyl ether; EWG, electron-withdrawing group; FBSM, 1-fluorobis(phenylsulfonyl)methane; HFiPA, 1,1,1,3,3,3-hexafluoro-2-propyl acrylate; LAH, lithium aluminum hydride; LG, leaving group; Moc, methyloxycarbonyl; MPEG, poly(ethylene glycol) monomethyl ether; MS, molecular sieves; MVK, methyl vinyl ketone; NFSI, N-fluorobenzenesulfonimide; NMR, nuclear magnetic resonance; Ns, p-nitrophenylsulfonyl; PEG, poly(ethylene glycol); PS, proton sponge [1,8-bis(dimethylamino)naphthalene]; rds, rate-determining step; TBAF, tetrabutylammonium fluoride; TCCA, trichloroisocyanuric acid; TFAA, trifluoroacetic anhydride; THF, tetrahydrofuran; TMAF, tetramethylammonium fluoride; TMS, trimethylsilyl; Ts, p-toluenesulfonyl; UNCA, urethane-protected α-amino acid N-carboxyanhydrides.
Key words
cinchona alkaloids - organocatalysis - asymmetric catalysis - kinetic resolution - stereoselective synthesis
- 1
Kaufman TS.Ruveda EA. Angew. Chem. Int. Ed. 2005, 44: 854 - 2
Cinchona Alkaloids in Synthesis
and Catalysis: Ligands, Immobilization and Organocatalysis
Song CE. Wiley-VCH; Weinheim: 2009. -
3a
Cozzi F. Adv. Synth. Catal. 2006, 348: 1367 -
3b
Benaglia M. New J. Chem. 2006, 30: 1525 -
4a
Dijkstra GDH.Kellogg RM.Wynberg H. Recl. Trav. Chim. Pays-Bas 1989, 108: 95 -
4b
Dijkstra GDH.Kellogg RM.Wynberg H.Svendsen JS.Marko I.Sharpless KB. J. Am. Chem. Soc. 1989, 111: 8069 -
4c
Bürgi T.Baiker A. J. Am. Chem. Soc. 1998, 120: 12920 -
4d
Olsen RA.Borchardt D.Mink L.Agarwal A.Mueller LJ.Zaera F. J. Am. Chem. Soc. 2006, 128: 15594 -
7a
Dondoni A.Massi A. Angew. Chem. Int. Ed. 2008, 47: 4638 -
7b
Pellissier H. Tetrahedron 2007, 63: 9267 -
7c
Enantioselective
Organocatalysis: Reactions and Experimental Procedures
Dalko PI. Wiley-VCH; Weinheim: 2007. -
7d
Gaunt MJ.Johansson CCC.McNally A.Vo NT. Drug Discovery Today 2007, 12: 8 -
7e
Seayad J.List B. Org. Biomol. Chem. 2005, 3: 719 -
7f
Berkessel A.Groger H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis Wiley-VCH; Weinheim: 2005. -
7g
Dalko PI.Moisan L. Angew. Chem. Int. Ed. 2004, 43: 5138 - 8
Yoon TP.Jacobsen EN. Science 2003, 299: 1691 -
9a
Pracejus H. Fortschr. Chem. Forsch. 1967, 8: 493 -
9b
Morrison JD.Mosher HS. Asymmetric Organic Reactions Prentice-Hall; Englewood Clifts: 1971. -
9c
Wynberg H. Top. Stereochem. 1986, 16: 87 - 10
Kacprzak K.Gawronski J. Synthesis 2001, 961 - 11
Marcelli T.Van Maarseveen JH.Hiemstra H. Angew. Chem. Int. Ed. 2006, 45: 7496 - For general reviews on asymmetric aminocatalysis, see:
-
12a
Melchiorre P.Marigo M.Carlone A.Bartoli G. Angew. Chem. Int. Ed. 2008, 47: 6138 -
12b
List B. Chem. Commun. 2006, 819 -
12c
List B. Synlett 2001, 1675 -
13a
Doyle AG.Jacobsen EN. Chem. Rev. 2007, 107: 5713 -
13b
Taylor MS.Jacobsen EN. Angew. Chem. Int. Ed. 2006, 45: 1520 -
14a
Chen Y. Synlett 2008, 1919 -
14b
Bartoli G.Melchiorre P. Synlett 2008, 1759 -
15a
Connon SJ. Synlett 2009, 354 -
15b
Connon SJ. Chem. Commun. 2008, 2499 - 16
Ooi T.Maruoka K. Angew. Chem. Int. Ed. 2007, 46: 4222 -
17a
Lygo B.Andrews BI. Acc. Chem. Res. 2004, 37: 518 -
17b
O’Donnell MJ. Acc. Chem. Res. 2004, 37: 506 -
17c
O’Donnell MJ. Aldrichimica Acta 2001, 34: 3 - For reviews, see:
-
18a
Sundermeier U.Döbler C.Beller M. In Modern Oxidation MethodsBäckvall JE. Wiley-VCH; Weinheim: 2004. -
18b
Bolm C.Hildebrand JP.Muniz K. In Catalytic Asymmetric Synthesis 2nd ed.:Ojima I. Wiley-VCH; Weinheim: 2000. -
18c
Kolb HC.Van Nieuwenhze MS.Sharpless KB. Chem. Rev. 1994, 94: 2483 -
19a
Tian SK.Chen YG.Hang JF.Tang L.Mcdaid P.Deng L. Acc. Chem. Res. 2004, 37: 621 -
19b
France S.Guerin DJ.Miller SJ.Lectka T. Chem. Rev. 2003, 103: 2985 - For reviews, see:
-
20a
Denmark SE.Beutner GL. Angew. Chem. Int. Ed. 2008, 47: 1560 -
20b
Fu GC. Acc. Chem. Res. 2004, 37: 542 -
20c
Miller SJ. Acc. Chem. Res. 2004, 37: 601 -
21a
Paull DH.Abraham CJ.Scerba MT.Alden-Danforth E.Lectka T. Acc. Chem. Res. 2008, 41: 655 -
21b
Ma JA.Cahard D. Angew. Chem. Int. Ed. 2004, 43: 4566 - 22
Enders D.Grondal C.Hüttl MRM. Angew. Chem. Int. Ed. 2007, 46: 1570 - 23
Guillena G.Ramón DJ.Yus M. Tetrahedron: Asymmetry 2007, 18: 693 - 24 For a review, see:
Bella M.Gasperi T. Synthesis 2009, 1583 - 25 For a review, see:
De Figueiredo RM.Christmann M. Eur. J. Org. Chem. 2007, 2575 -
26a
Hajos ZG, andParrish DR. inventors; German patent 2102623. -
26b
Hajos ZG.Parrish DR. J. Org. Chem. 1974, 39: 1615 -
26c
Eder U.Sauer G.Wiechert R. Angew. Chem., Int. Ed. Engl. 1971, 10: 496 - 27
List B.Lerner RA.Barbas CF. J. Am. Chem. Soc. 2000, 122: 2395 - For reviews on the use of α-amino acids and their derivatives in aldol and related reactions, see:
-
28a
Guillena G.Nájera C.Ramón DJ. Tetrahedron: Asymmetry 2007, 18: 2249 -
28b
Notz W.Tanaka F.Barbas CF. Acc. Chem. Res. 2004, 37: 580 -
28c
List B. Tetrahedron 2002, 58: 5573 - 29
Bluet G.Campagne JM. J. Org. Chem. 2001, 66: 4293 -
30a
Mettath S.Srikanth GSC.Dangerfield BS.Castle SL. J. Org. Chem. 2004, 69: 6489 -
30b
Ma B.Parkinson JL.Castle SL. Tetrahedron Lett. 2007, 48: 2083 - 31
Andrus MB.Liu J.Ye ZF.Cannon JF. Org. Lett. 2005, 7: 3861 - 32
Markert M.Mulzer M.Schetter B.Mahrwald R. J. Am. Chem. Soc. 2007, 129: 7258 - 33
Ogawa S.Shibata N.Inagaki J.Nakamura S.Toru T.Shiro M. Angew. Chem. Int. Ed. 2007, 46: 8666 - 34
Zheng BL.Liu QZ.Guo CS.Wang XL.He L. Org. Biomol. Chem. 2007, 5: 2913 - 35
Orsini F.Pelizzoni F.Forte M.Destro R.Gariboldi P. Tetrahedron 1988, 44: 519 - 36
Chen J.An X.Zhu X.Wang X.Xiao W. J. Org. Chem. 2008, 73: 6006 - 37
Zhou J.Wakchaure V.Kraft P.List B. Angew. Chem. Int. Ed. 2008, 47: 7656 -
38a
Agami C.Sevestre H. J. Chem. Soc., Chem. Commun. 1984, 1385 -
38b
Agami C.Platzer N.Sevestre H. Bull. Soc. Chim. Fr. 1987, 2: 358 - 39 For a recent review of the asymmetric
MBH and aza-MBH, see:
Masson G.Housseman C.Zhu J. Angew. Chem. Int. Ed. 2007, 46: 4614 -
40a
Morita K.Suzuki Z.Hirose H. Bull. Chem. Soc. Jpn. 1968, 41: 2815 -
40b
Baylis AB, andHillman MED. inventors; German Patent 2155113. - For general reviews about the(aza)-MBH reaction and further manipulation of the products, see:
-
41a
Singh V.Batra S. Tetrahedron 2008, 64: 4511 -
41b
Basavaiah D.Rao KV.Reddy RJ. Chem. Soc. Rev. 2007, 35: 1581 -
41c
Lee KY.Gowrisankar S.Kim JN. Bull. Korean Chem. Soc. 2005, 26: 1481 -
41d
Basavaiah D.Rao AJ.Satyanarayana T. Chem. Rev. 2003, 103: 811 -
42a
Robiette R.Aggarwal VK.Harvey JN. J. Am. Chem. Soc. 2007, 129: 15513 -
42b
Buskens P.Klankermayer J.Leitner W. J. Am. Chem. Soc. 2005, 127: 16762 -
42c
Price KE.Broadwater SJ.Walker BJ.McQuade DT. J. Org. Chem. 2005, 70: 3980 -
42d
Aggarwal VK.Fulford SY.Lloyd-Jones GC. Angew. Chem. Int. Ed. 2005, 44: 1706 -
42e
Price KE.Broadwater SJ.Jung HM.McQuade DT. Org. Lett. 2005, 7: 147 -
42f
Santos LS.Pavam CH.Almeida WP.Coelho F.Eberlin MN. Angew. Chem. Int. Ed. 2004, 43: 4330 - 43
Markó IE.Giles PR.Hindley NJ. Tetrahedron 1997, 53: 1015 -
44a
Iwabuchi Y.Nakatani M.Yokoyama N.Hatakeyama S. J. Am. Chem. Soc. 1999, 121: 10219 -
44b
Nakano A.Kawahara S.Akamatsu S.Morokuma K.Nakatani M.Iwabuchi Y.Takahashi K.Ishihara J.Hatakeyama S. Tetrahedron 2006, 62: 381 -
45a
Iwabuchi Y.Furukawa M.Esumi T.Hatakeyama S. Chem. Commun. 2001, 2030 -
45b
Iwabuchi Y.Sugihara T.Esumi T.Hatakeyama S. Tetrahedron Lett. 2001, 42: 7867 - 46
Shi M.Jiang JK. Tetrahedron: Asymmetry 2002, 13: 1941 - Selected examples:
-
47a
Tang H.Zhao G.Zhou Z.Gao P.He L.Tang C. Eur. J. Org. Chem. 2008, 126 -
47b
Lattanzi A. Synlett 2007, 2106 -
47c
Vasbinder MM.Imbriglio JE.Miller SJ. Tetrahedron 2006, 62: 11450 -
47d
Wang J.Li H.Yu X.Zu L.Wang W. Org. Lett. 2005, 7: 4293 -
47e
Aroyan CE.Vasbinder MM.Miller SJ. Org. Lett. 2005, 7: 3849 -
47f
Krishna PR.Kannan V.Reddy PVN. Adv. Synth. Catal. 2004, 346: 603 - For general reviews, see:
-
48a
Palomo C.Oiarbide M.Laso A. Eur. J. Org. Chem. 2007, 2561 -
48b
Palomo C.Oiarbide M.Mielgo A. Angew. Chem. Int. Ed. 2004, 41: 5442 -
48c
Luzzio FA. Tetrahedron 2001, 57: 915 -
48d
Rosini G. In Comprehensive Organic Synthesis Vol. 2:Trost BM.Fleming I.Heathcock CH. Pergamon; New York: 1991. p.321 - 49
Ono N. The Nitro Group in Organic Synthesis Wiley-VCH; New York: 2001. - Selected examples:
-
50a
Sasai H.Suzuki T.Arai S.Shibasaki M. J. Am. Chem. Soc. 1992, 114: 4418 -
50b
Shibasaki M.Yoshikawa N. Chem. Rev. 2002, 102: 2187 -
50c
Trost B.Yeh VSC. Angew. Chem. Int. Ed. 2002, 41: 861 -
50d
Trost B.Yeh VSC.Ito H.Bremeyer N. Org. Lett. 2002, 4: 2621 -
50e
Evans DA.Seidel D.Rueping M.Lam HW.Shaw JT.Downey CW. J. Am. Chem. Soc. 2003, 125: 12692 -
50f
Palomo C.Oiarbide M.Laso A. Angew. Chem. Int. Ed. 2005, 44: 3881 - 51 Next to the developments described
in this section, Nagasawa et al. obtained up to 92% ee
in the Henry reaction of α-branched aldehydes and nitromethane
using guanidine/thiourea catalysts:
Sohtome Y.Hashimoto Y.Nagasawa K. Adv. Synth. Catal. 2005, 347: 1643 - 52
Misumi Y.Bulman RA.Matsumoto K. Heterocycles 2002, 56: 599 -
53a
Marcelli T.van der Haas RNS.van Maarseveen JH.Hiemstra H. Synlett 2005, 2817 -
53b
Marcelli T.
van der Haasvan Maarseveen JH.Hiemstra H. Angew. Chem. Int. Ed. 2006, 45: 929 - For reviews about the use of(thio)ureas in organic catalysis, see:
-
54a
Miyabe H.Takemoto Y. Bull. Chem. Soc. Jpn. 2008, 81: 785 -
54b
Ref. 15b.
-
54c
Yu X.Wang W. Chem. Asian J. 2008, 3: 516 -
54d
Doyle AG.Jacobsen EN. Chem. Rev. 2007, 107: 5759 -
54e
Connon SJ. Chem. Eur. J. 2006, 12: 5419 - 55
Hammar P.Marcelli T.Hiemstra H.Himo F. Adv. Synth. Catal. 2007, 349: 2537 - 56
Li HM.Wang BM.Deng L. J. Am. Chem. Soc. 2006, 128: 732 -
57a
Mandal T.Samanta S.Zhao CG. Org. Lett. 2007, 9: 943 -
57b
Samanta S.Zhao CG. ARKIVOC 2007, (xiii): 218 - 58
Bandini M.Sinisi R.Umani-Ronchi A. Chem. Commun. 2008, 4360 - For reviews, see:
-
59a
Khan NH.Kureshy RI.Abdi SH.Agrawal S.Jasra RV. Coord. Chem. Rev. 2008, 252: 593 -
59b
Brunel J.Holmes IP. Angew. Chem. Int. Ed. 2004, 43: 2752 -
59c
North M. Tetrahedron: Asymmetry 2003, 14: 147 -
59d
Gregory R. Chem. Rev. 1999, 99: 3649 - For reviews, see:
-
60a
Purkarthofer T.Skranc W.Schuster C.Griengl H. Appl. Microbiol. Biotechnol. 2007, 76: 309 -
60b
Sharma M.Sharma NN.Bhalla TC. Enzym. Microb. Technol. 2005, 37: 279 -
60c
Griengl H.Schwab H.Fechter M. Trends Biotechnol. 2000, 18: 252 -
61a
Tian S.Deng L. J. Am. Chem. Soc. 2001, 123: 6195 -
61b
Tian SK.Deng L. Tetrahedron 2006, 62: 11320 - 62
Chinchilla R.Nájera C.Ortega FJ. Tetrahedron: Asymmetry 2008, 19: 265 - 63
Choi MCK.Chan SS.Chan MK.Kim JC.Matsumoto K. Heterocycles 2002, 58: 645 - 64
Tian SK.Hong R.Deng L. J. Am. Chem. Soc. 2003, 125: 9900 - For reviews, see:
-
65a
Poulsen TB.Jørgensen KA. Chem. Rev. 2008, 108: 2903 -
65b
Bandini M.Melloni A.Umani-Ronchi A. Angew. Chem. Int. Ed. 2004, 43: 550 - 66
Török B.Abid M.London G.Esquibel J.Torok M.Mhadgut SC.Yan P.Prakash GKS. Angew. Chem. Int. Ed. 2005, 44: 3086 - 67
Li HM.Wang YQ.Deng L. Org. Lett. 2006, 8: 4063 - 68
Zhao J.Liu L.Gu C.Wang D.Chen Y. Tetrahedron Lett. 2008, 49: 1476 - For recent reviews, see:
-
69a
Hagmann WK. J. Med. Chem. 2008, 51: 4359 -
69b
Muller K.Faeh C.Diederich F. Science 2007, 317: 1881 -
69c
Kirk KL. Org. Process Res. Dev. 2008, 12: 305 -
69d
Böhm H.Banner D.Bendels S.Kansy M.Kuhn B.Müller K.Obst-Sander U.Stahl M. ChemBioChem 2004, 5: 637 - For recent reviews, see:
-
70a
Brunet V.O’Hagan D. Angew. Chem. Int. Ed. 2008, 47: 1179 -
70b
Ma J.Cahard D.
J. Fluorine Chem. 2007, 128: 975 -
70c
Billard T.Langlois BR. Eur. J. Org. Chem. 2007, 891 -
70d
Bobbio C.Gouverneur V. Org. Biomol. Chem. 2006, 4: 2065 -
70e
Ma J.Cahard D. Chem. Rev. 2004, 104: 6119 - 71
Iseki K.Nagai T.Kobayashi Y. Tetrahedron Lett. 1994, 35: 3137 - 72
Caron S.Do NM.Arpin P.Larivee A. Synthesis 2003, 1693 - 73
Hu X.Wang J.Li W.Lin L.Liu X.Feng X. Tetrahedron Lett. 2009, 50: 4378 - 74
Nagao H.Kawano Y.Mukaiyama T. Bull. Chem. Soc. Jpn. 2007, 80: 2406 -
75a
Mizuta S.Shibata N.Hibino M.Nagano S.Nakamura S.Toru T. Tetrahedron 2007, 63: 8521 -
75b
Mizuta S.Shibata N.Akiti S.Fujimoto H.Nakamura S.Toru T. Org. Lett. 2007, 9: 3707 -
76a
Calter MA.Zhu C. Org. Lett. 2002, 4: 205 -
76b
Calter MA.Zhu C.Lachicotte RJ. Org. Lett. 2002, 4: 209 -
76c
Dunlop AP.Hurd CD. J. Org. Chem. 1950, 15: 1160 -
76d
Canton IJ.Cocker W.McMurry TBH. Tetrahedron 1961, 15: 45 - 77
Calter MA.Phillips RM.Flaschenriem C. J. Am. Chem. Soc. 2005, 127: 14566 -
78a
Jin Y.Liu XY.Jing LL.He W.Sun XL.Zhang SY. Chirality 2007, 19: 386 -
78b
Jin Y.Yao ZJ.Liu P.Jiang R.Zhang SY. Chin. J. Org. Chem. 2008, 28: 94 -
78c
Chen H.Jin Y.Jiang R.Sun X.Li X.Zhang S. Catal. Commun. 2008, 9: 1858 - For general reviews, see:
-
79a
Friestad GK.Mathies AK. Tetrahedron 2007, 63: 2541 -
79b
Vilaivan T.Bhanthumnavin W.Sritana-Anant Y. Curr. Org. Chem. 2005, 9: 1315 -
79c
Córdova A. Acc. Chem. Res. 2004, 37: 102 - For reviews on organocatalytic Mannich reactions, see:
-
80a
Verkade JMM.Hemert LJCV.Quaedflieg PJLM.Rutjes FPJT. Chem. Soc. Rev. 2008, 37: 29 -
80b
Ting A.Schaus SE. Eur. J. Org. Chem. 2007, 5797 -
81a
Lou S.Taoka BM.Ting A.Schaus SE. J. Am. Chem. Soc. 2005, 127: 11256 -
81b
Goss JM.Schaus SE. J. Org. Chem. 2008, 73: 7651 - 82
Poulsen TB.Alemparte C.Saaby S.Bella M.Jørgensen KA. Angew. Chem. Int. Ed. 2005, 44: 2896 - 83
Song J.Wang Y.Deng L. J. Am. Chem. Soc. 2006, 128: 6048 - 84
Bode CA.Ting A.Schaus SE. Tetrahedron 2006, 62: 11499 - 85
Tillman AL.Ye JX.Dixon DJ. Chem. Commun. 2006, 1191 -
86a
Ting A.Lou S.Schaus SE. Org. Lett. 2006, 8: 2003 -
86b
Lou S.Dai P.Schaus SE. J. Org. Chem. 2007, 72: 9998 - 87
Marianacci O.Micheletti G.Bernardi L.Fini F.Fochi M.Pettersen D.Sgarzani V.Ricci A. Chem. Eur. J. 2007, 13: 8338 - 88
Song J.Shih HW.Deng L. Org. Lett. 2007, 9: 603 - 89
Cheng L.Liu L.Jia H.Wang D.Chen Y. J. Org. Chem. 2009, 74: 4650 - 90
Li L.Ganesh M.Seidel D. J. Am. Chem. Soc. 2009, 131: 11648 - 91
Ricci A.Pettersen D.Bernardi L.Fini F.Fochi M.Herrera RP.Sgarzani V. Adv. Synth. Catal. 2007, 349: 1037 -
92a
Fortner KC.Shair MD. J. Am. Chem. Soc. 2007, 129: 1032 -
92b
Magdziak D.Lalic G.Lee HM.Fortner KC.Aloise AD.Shair MD. J. Am. Chem. Soc. 2005, 127: 7284 -
92c
Lalic G.Aloise AD.Shair MD. J. Am. Chem. Soc. 2003, 125: 2852 -
92d
Orlandi S.Benaglia M.Cozzi F. Tetrahedron Lett. 2004, 45: 1747 - For recent reviews, see:
-
93a
Shi Y.-L.Shi M. Eur. J. Org. Chem. 2007, 2905 -
93b
Ref. 39.
-
93c
Ref. 41.
-
94a
Shi M.Xu Y. Angew. Chem. Int. Ed. 2002, 41: 4507 -
94b
Shi M.Xu YM.Shi YL. Chem. Eur. J. 2005, 11: 1794. In both articles the assignment of the absolute configuration of the aza-MBH products is erroneous - 95
Balan D.Adolfsson H. Tetrahedron Lett. 2003, 44: 2521. Also in this case the absolute configurations are incorrect - 96
Kawahara S.Nakano A.Esumi T.Iwabuchi Y.Hatakeyama S. Org. Lett. 2003, 5: 3103 - 97
Shi M.Zhao G.-L. Adv. Synth. Catal. 2004, 346: 1205 - 98
Abermil N.Masson G.Zhu J. J. Am. Chem. Soc. 2008, 130: 12596 - For reviews, see:
-
99a
Westermann B. Angew. Chem. Int. Ed. 2003, 42: 151 -
99b
Ref. 48.
-
100a
Knudsen KR.Jørgensen KA. Org. Biomol. Chem. 2005, 3: 1362 - For related studies using only copper catalysis, see:
-
100b
Knudsen KR.Risgaard T.Nishiwaki N.Gothelf KV.Jørgensen KA. J. Am. Chem. Soc. 2001, 123: 5843 -
100c
Nishiwaki N.Knudsen KR.Gothelf KV.Jørgensen KA. Angew. Chem. Int. Ed. 2001, 40: 2992 -
101a
Palomo C.Oiarbide M.Laso A.López R. J. Am. Chem. Soc. 2005, 127: 17622 -
101b
Gomez-Bengoa E.Linden A.López R.Mugica-Mendiola I.Oiarbide M.Palomo C. J. Am. Chem. Soc. 2008, 130: 7955 - 102
Fini F.Sgarzani V.Pettersen D.Herrera RP.Bernardi L.Ricci A. Angew. Chem. Int. Ed. 2005, 44: 7975 - 103
Bernardi L.Fini F.Herrera RP.Ricci A.Sgarzani V. Tetrahedron 2006, 62: 375 - For recent reviews, see:
-
104a
Spino C. Angew. Chem. Int. Ed. 2004, 43: 1764 -
104b
Gröger H. Chem. Rev. 2003, 103: 2795 -
104c
Yet L. Angew. Chem. Int. Ed. 2001, 40: 875 - Selected examples:
-
105a
Sigman MS.Jacobsen EN.
J. Am. Chem. Soc. 1998, 120: 4901 -
105b
Iyer MS.Gigstad KM.Namdev ND.Lipton MA. J. Am. Chem. Soc. 1996, 118: 4910 -
105c
Corey EJ.Grogan MJ. Org. Lett. 1999, 1: 157 -
106a
Huang J.Corey EJ. Org. Lett. 2003, 5: 3455 -
106b
Huang J.Corey EJ. Org. Lett. 2004, 6: 5027 - 107
Wang J.Hu XL.Jiang J.Gou SH.Huang X.Liu XH.Feng XM. Angew. Chem. Int. Ed. 2007, 46: 8468 - Selected examples:
-
108a
Uraguchi D.Sorimachi K.Terada M. J. Am. Chem. Soc. 2004, 126: 11804 -
108b
Terada M.Yokoyama S.Sorimachi K.Uraguchi D. Adv. Synth. Catal. 2007, 349: 1863 -
108c
Kang Q.Zhao Z.-A.You S.-L. J. Am. Chem. Soc. 2007, 129: 1484 -
108d
Rowland GB.Rowland EB.Liang Y.Perman JA.Antilla JC. Org. Lett. 2007, 9: 2609 -
108e
Li G.Rowland GB.Rowland EB.Antilla JC. Org. Lett. 2007, 9: 4065 - 109
Wang YQ.Song J.Hong R.Li HM.Deng L. J. Am. Chem. Soc. 2006, 128: 8156 - 110
Yu P.He J.Yang L.Pu M.Guo X. J. Catal. 2008, 260: 81 - 111
Yu P.He J.Guo C. Chem. Commun. 2008, 2355 - For reviews, see:
-
112a
Hiratake J.Oda J. Biosci., Biotechnol., Biochem. 1997, 61: 211 -
112b
Kafarski P.Lejczak B. Phosphorus, Sulfur Silicon 1991, 63: 193 -
112c
Kaplan AP.Bartlett PA. Biochemistry 1991, 30: 8165 -
112d
Aminophosphonic
and Aminophosphinic Acids
Kukhar VP.Hudson HR. John Wiley & Sons; New York: 2000. -
113a
Wynberg H.Smaardijk AA. Tetrahedron Lett. 1983, 24: 5899 -
113b
Smaardijk AA.Noorda S.van Bolhuis F.Wynberg H. Tetrahedron Lett. 1985, 26: 493 -
114a
Sasai H.Arai S.Tahara Y.Shibasaki M. J. Org. Chem. 1995, 60: 6656 -
114b
Gröger H.Saida Y.Arai S.Martens J.Sasai H.Shibasaki M. Tetrahedron Lett. 1996, 37: 9291 -
114c
Gröger H.Saida Y.Sasai H.Yamaguchi K.Martens J.Shibasaki M. J. Am. Chem. Soc. 1998, 120: 3089 -
114d
Saida Y.Gröger H.Maison W.Durot N.Sasai H.Shibasaki M.Martens J. J. Org. Chem. 2000, 65: 4818 -
115a
Joly GD.Jacobsen EN. J. Am. Chem. Soc. 2004, 126: 4102 -
115b
Akiyama T.Morita H.Itoh J.Fuchibe K. Org. Lett. 2005, 7: 2583 - 116
Pettersen D.Marcolini M.Bernardi L.Fini F.Herrera RP.Sgarzani V.Ricci A. J. Org. Chem. 2006, 71: 6269 - 117
Nakamura S.Nakashima H.Yamamura A.Shibata N.Toru T. Adv. Synth. Catal. 2008, 350: 1209 - For reviews, see:
-
118a
Sani M.Sinisi R.Molteni M.Jagodzinska M.Huguenot F.Bruché L.Zanda M. Chim. Oggi - Chem. Today 2006, 24: 42 -
118b
Zanda M. New J. Chem. 2004, 28: 1401 - 119
Mizuta S.Shibata N.Goto Y.Furukawa T.Nakamura S.Toru T. J. Am. Chem. Soc. 2007, 129: 6394 - 120
Kawai H.Kusuda A.Nakamura S.Shiro M.Shibata N. Angew. Chem. Int. Ed. 2009, 48: 6324 - For reviews, see:
-
121a
Tsogoeva SB. Eur. J. Org. Chem. 2007, 1701 -
121b
Almasi D.Alonso DA.Najera C. Tetrahedron: Asymmetry 2007, 18: 299 -
121c
Vicario JL.Badia D.Carrillo L. Synthesis 2007, 2065 -
122a
Kim DY.Huh SC. Tetrahedron 2001, 57: 8933 -
122b
Kim DY.Huh SC.Kim SM. Tetrahedron Lett. 2001, 42: 6299 -
122c
Cho MJ.Cho MG.Huh SC.Kim SM.Lee K.Koh KO.Mang JY.Kim DY. Bull. Korean Chem. Soc. 2006, 27: 857 -
123a
Vakulya B.Varga S.Csampai A.Soós T. Org. Lett. 2005, 7: 1967 -
123b
Vakulya B.Varga S.Soós T. J. Org. Chem. 2008, 73: 3475 - 124
Corey EJ.Zhang F. Org. Lett. 2000, 2: 4257 - 125
Tárkányi G.Király P.Varga S.Vakulya B.Soós T. Chem. Eur. J. 2008, 14: 6078 - 126 For a discussion on organocatalysts
self-association, see:
Marcelli T. In Advances in Synthetic ChemistryPignataro B. Wiley-VCH; Weinheim: 2010. - 127
Lu H.Wang X.Yao C.Zhang J.Wu H.Xiao W. Chem. Commun. 2009, 4251 - 128
Li P.Wang Y.Liang X.Ye J. Chem. Commun. 2008, 3302 - 129
Wang J.Li H.Zu LS.Jiang W.Xie HX.Duan WH.Wang W. J. Am. Chem. Soc. 2006, 128: 12652 - 130
Gu CL.Liu L.Sui Y.Zhao JL.Wang D.Chen YJ. Tetrahedron: Asymmetry 2007, 18: 455 - 131
Paixão MW.Holub N.Vila C.Nielsen M.Jørgensen K. Angew. Chem. Int. Ed. 2009, 48: 7338 - 132
Szöllösi G.Bartók M. Chirality 2001, 13: 614 - 133
Bonfils F.Cazaux I.Hodge P.Caze C. Org. Biomol. Chem. 2006, 4: 493 - 134
Dere RT.Pal RR.Patil PS.Salunkhe MM. Tetrahedron Lett. 2003, 44: 5351 - 135
Shi J.Wang M.He L.Zheng K.Liu X.Lin L.Feng X. Chem. Commun. 2009, 4711 - 136
Furukawa T.Shibata N.Mizuta S.Nakamura S.Toru T.Shiro M. Angew. Chem. Int. Ed. 2008, 47: 8051 - 137
Moon HW.Cho MJ.Kim DY. Tetrahedron Lett. 2009, 50: 4896 - 138
Onimura K.Matsuzaki K.Lee Yk.Tsutsumi H.Oishi T. Polym. J. 2004, 36: 190 - 139
Wu FH.Li HM.Hong R.Deng L. Angew. Chem. Int. Ed. 2006, 45: 947 - 140
Rigby CL.Dixon DJ. Chem. Commun. 2008, 3798 - 141
Wu FH.Hong R.Khan JH.Liu XF.Deng L. Angew. Chem. Int. Ed. 2006, 45: 4301 -
142a
Mayer S.List B. Angew. Chem. Int. Ed. 2006, 45: 4193 -
142b
Martin NJA.List B. J. Am. Chem. Soc. 2006, 128: 13368 -
142c
Zhou J.List B. J. Am. Chem. Soc. 2007, 129: 7498 -
142d
Wang X.List B. Angew. Chem. Int. Ed. 2008, 47: 1119 - 143
Bartoli G.Bosco M.Carlone A.Pesciaioli F.Sambri L.Melchiorre P. Org. Lett. 2007, 9: 1403 -
144a
Bartoli G.Bosco M.Carlone A.Cavalli A.Locatelli M.Mazzanti A.Ricci P.Sambri L.Melchiorre P. Angew. Chem. Int. Ed. 2006, 45: 4966 -
144b
Cucinotta CS.Kosa M.Melchiorre P.Cavalli A.Gervasio F. Chem. Eur. J. 2009, 15: 7913 - 145 For a review, see:
Cui H.Chen Y. Chem. Commun. 2009, 4479 - 146
Lu J.Zhou W.Liu F.Loh T. Adv. Synth. Catal. 2008, 350: 1796 -
147a
Xie JW.Chen W.Li R.Zeng M.Du W.Yue L.Chen YC.Wu Y.Zhu J.Deng JG. Angew. Chem. Int. Ed. 2007, 46: 389 -
147b
Kang T.Xie J.Du W.Feng X.Chen Y. Org. Biomol. Chem. 2008, 6: 2673 - 148
Wu ZJ.Luo SW.Xie JW.Xu XY.Fang DM.Zhang GL. J. Am. Soc. Mass Spectrom. 2007, 18: 2074 -
149a
Li XF.Cun LF.Lian CX.Zhong L.Chen YC.Liao J.Zhu J.Deng JG. Org. Biomol. Chem. 2008, 6: 349 -
149b
Chen W.Du W.Yue L.Li R.Wu Y.Ding LS.Chen YC. Org. Biomol. Chem. 2007, 5: 816 - 150
Bell M.Frisch K.Jørgensen KA. J. Org. Chem. 2006, 71: 5407 -
151a
Alemán J.Jacobsen CB.Frisch K.Overgaard J.Jørgensen KA. Chem. Commun. 2008, 632 -
151b
Alemán J.Richter B.Jørgensen KA. Angew. Chem. Int. Ed. 2007, 46: 5515 - 152
Bella M.Jørgensen KA. J. Am. Chem. Soc. 2004, 126: 5672 - 153
Elsner P.Bernardi L.Salla G.Overgaard J.Jørgensen K. J. Am. Chem. Soc. 2008, 130: 4897 - 154
Bernardi L.Lopez-Cantarero J.Niess B.Jørgensen KA. J. Am. Chem. Soc. 2007, 129: 5772 - 155
O’Donnell MJ.Delgado F.Dominguez E.De Blas J.Scott WL. Tetrahedron: Asymmetry 2001, 12: 821 - 156
Chinchilla R.Mazon P.Najera C.Ortega FJ.Yus M. ARKIVOC 2005, (vi): 222 - 157
Andrus MB.Ye Z. Tetrahedron Lett. 2008, 49: 534 -
158a
Tozawa T.Yamane Y.Mukaiyama T. Chem. Lett. 2006, 35: 56 -
158b
Tozawa T.Nagao H.Yamane Y.Mukaiyama T. Chem. Asian J. 2007, 2: 123 -
158c
Nagao H.Yamane Y.Mukaiyama T. Heterocycles 2007, 72: 553 - 159
Calter MA.Wang J. Org. Lett. 2009, 11: 2205 - 160 For a recent review, see:
Nising CF.Bräse S. Chem. Soc. Rev. 2008, 37: 1218 - 161
Merschaert A.Delbeke P.Daloze D.Dive G. Tetrahedron Lett. 2004, 45: 4697 - 162
Biddle MM.Lin M.Scheidt KA. J. Am. Chem. Soc. 2007, 129: 3830 - 163
Dittmer C.Raabe G.Hintermann L. Eur. J. Org. Chem. 2007, 5886 - 164
Li DR.Murugan A.Falck JR. J. Am. Chem. Soc. 2008, 130: 46 - 165
Lu X.Liu Y.Sun B.Cindric B.Deng L. J. Am. Chem. Soc. 2008, 130: 8134 - 166
Carlone A.Bartoli G.Bosco M.Pesciaioli F.Ricci P.Sambri L.Melchiorre P. Eur. J. Org. Chem. 2007, 5492 - 167 For a review, see:
Enders D.Luttgen K.Narine AA. Synthesis 2007, 959 - 168
Hiemstra H.Wynberg H. J. Am. Chem. Soc. 1981, 103: 417 - 169
Athawale V.Manjrekar N. Tetrahedron Lett. 2001, 42: 4541 - 170
McDaid P.Chen YG.Deng L. Angew. Chem. Int. Ed. 2002, 41: 338 - 171
Liu Y.Sun B.Wang B.Wakem M.Deng L. J. Am. Chem. Soc. 2009, 131: 418 -
172a
Zu LS.Wang J.Li H.Xie HX.Jiang W.Wang W. J. Am. Chem. Soc. 2007, 129: 1036 -
172b
Zu L.Xie H.Li H.Wang J.Jiang W.Wang W. Adv. Synth. Catal. 2007, 349: 1882 - 173
Ricci P.Carlone A.Bartoli G.Bosco M.Sambri L.Melchiorre P. Adv. Synth. Catal. 2008, 350: 49 - 174
Perdicchia D.Jørgensen KA. J. Org. Chem. 2007, 72: 3565 - 175
Luo G.Zhang S.Duan W.Wang W. Synthesis 2009, 1564 - 176
McCooey SH.Connon SJ. Angew. Chem. Int. Ed. 2005, 44: 6367 -
177a
Ye JX.Dixon DJ.Hynes PS. Chem. Commun. 2005, 4481 -
177b
Hynes P.Stupple P.Dixon D. Org. Lett. 2008, 10: 1389 - 178
Li H.Zu L.Xie H.Wang W. Synthesis 2009, 1525 - 179
Malerich JP.Hagihara K.Rawal VH. J. Am. Chem. Soc. 2008, 130: 14416 - 180
Elsner P.Jiang H.Nielsen JB.Pasi F.Jørgensen KA. Chem. Commun. 2008, 5827 - 181
Kleczkowska E.Sas W. Pol. J. Chem. 2007, 81: 1457 -
182a
Li HM.Wang Y.Tang L.Deng L. J. Am. Chem. Soc. 2004, 126: 9906 -
182b
Li HM.Wang Y.Tang L.Wu FH.Liu XF.Guo CY.Foxman BM.Deng L. Angew. Chem. Int. Ed. 2005, 44: 105 - 183
Chen FX.Shao C.Wang Q.Gong P.Zhang DY.Zhang BZ.Wang R. Tetrahedron Lett. 2007, 48: 8456 - 184
Shi M.Lei ZY.Zhao MX.Shi JW. Tetrahedron Lett. 2007, 48: 5743 - 185
Wang J.Li H.Zua LS.Jiang W.Wang W. Adv. Synth. Catal. 2006, 348: 2047 - 186
Mandal T.Zhao C. Angew. Chem. Int. Ed. 2008, 47: 7714 - 187
Xue D.Chen YC.Wang QW.Cun LF.Zhu J.Deng JG. Org. Lett. 2005, 7: 5293 - 188
Poulsen TB.Bell M.Jørgensen KA. Org. Biomol. Chem. 2006, 4: 63 - 189
Lubkoll J.Wennemers H. Angew. Chem. Int. Ed. 2007, 46: 6841 - 190
Hynes PS.Stranges D.Stupple PA.Guarna A.Dixon DJ. Org. Lett. 2007, 9: 2107 - 191
Bernardi L.Fini F.Fochi M.Ricci A. Synlett 2008, 1857 - 192
McCooey SH.Connon SJ. Org. Lett. 2007, 9: 599 - 193
Tan B.Chua PJ.Li Y.Zhong G. Org. Lett. 2008, 10: 2437 - 194
Diner P.Nielsen M.Bertelsen S.Niess B.Jørgensen KA. Chem. Commun. 2007, 3646 - 195
Wang J.Xie H.Li H.Zu L.Wang W. Angew. Chem. Int. Ed. 2008, 47: 4177 - 196
Lu H.Zhang F.Meng X.Duan S.Xiao W. Org. Lett. 2009, 11: 3946 - 197
Wang J.Li H.Zu LS.Wang W. Org. Lett. 2006, 8: 1391 - 198
Nielsen M.Zhuang W.Jørgensen KA. Tetrahedron 2007, 63: 5849 - 199
Bartoli G.Bosco M.Carlone A.Locatelli M.Mazzanti A.Sambri L.Melchiorre P. Chem. Commun. 2007, 722 - 200
Wang J.Heikkinen LD.Li H.Zu LS.Jiang W.Xie HX.Wang W. Adv. Synth. Catal. 2007, 349: 1052 - 201
Cann P.Levacher V.Bourguignon J.Dupas G. Lett. Org. Chem. 2004, 1: 129 -
202a
Wang Y.Liu XF.Deng L. J. Am. Chem. Soc. 2006, 128: 3928 -
202b
Wang BM.Wu FH.Wang Y.Liu XF.Deng L. J. Am. Chem. Soc. 2007, 129: 768 - 203
Yue L.Du W.Liu Y.Chen Y. Tetrahedron Lett. 2008, 49: 3881 - 204
Li HM.Song J.Liu XF.Deng L. J. Am. Chem. Soc. 2005, 127: 8948 - 205
Zhu Q.Cheng L.Lu Y. Chem. Commun. 2008, 6315 - 206
Capuzzi M.Perdicchia D.Jørgensen KA. Chem. Eur. J. 2008, 14: 128 - 207
Pihko PM.Pohjakallio A. Synlett 2004, 2115 - 208
Saaby S.Bella M.Jørgensen KA. J. Am. Chem. Soc. 2004, 126: 8120 -
209a
Liu XF.Li HM.Deng L. Org. Lett. 2005, 7: 167 -
209b
Liu X.Sun B.Deng L. Synlett 2009, 1685 - 210
Poulsen TB.Alemparte C.Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 11614 -
211a
Brandes S.Bella M.Kjoersgaard A.Jørgensen KA. Angew. Chem. Int. Ed. 2006, 45: 1147 -
211b
Brandes S.Niess B.Bella M.Prieto A.Overgaard J.Jørgensen KA. Chem. Eur. J. 2006, 12: 6039 -
212a
Liu TY.Cui HL.Zhang Y.Jiang K.Du W.He ZQ.Chen Y. Org. Lett. 2007, 9: 3671 -
212b
Cheng L.Liu L.Wang D.Chen Y. Org. Lett. 2009, 11: 3874 - For reviews, see:
-
213a
Lattanzi A. Curr. Org. Synth. 2008, 5: 117 -
213b
Wong OA.Shi Y. Chem. Rev. 2008, 108: 3958 -
214a
Lygo B.To DCM. Tetrahedron Lett. 2001, 42: 1343 -
214b
Lygo B.Wainwright PG. Tetrahedron Lett. 1998, 39: 1599 -
214c
Lygo B.Wainwright PG. Tetrahedron 1999, 55: 6289 -
214d
Lygo B.Gardiner SD.Mcleod MC.To DCM. Org. Biomol. Chem. 2007, 5: 2283 - 215 For a report describing an attempt
on a 3-styrylchromone, see:
Patonay T.Kiss-Szikszai A.Silva VML.Silva AMS.Pinto DCGA.Cavaleiro JAS.Jekó J. Eur. J. Org. Chem. 2008, 1937 - 216
Lygo B.Gardiner SD.To DCM. Synlett 2006, 2063 - 217
Lygo B.To DCM. Chem. Commun. 2002, 2360 -
218a
Ye JX.Wang YC.Liu RH.Zhang GF.Zhang Q.Chen JP.Liang XM. Chem. Commun. 2003, 2714 -
218b
Wang YC.Ye JX.Liang XM. Adv. Synth. Catal. 2007, 349: 1033 - 219
Dorow RL.Tymonko SA. Tetrahedron Lett. 2006, 47: 2493 - 220
Jew S.Lee JH.Jeong BS.Yoo MS.Kim MJ.Lee YJ.Lee J.Choi SH.Lee K.Lah MS.Park H. Angew. Chem. Int. Ed. 2005, 44: 1383 - 221
Liu XD.Bai XL.Qiu XP.Gao LX. Chin. Chem. Lett. 2005, 16: 975 - 222
Lv J.Wang X.Liu JY.Z hang LP.Wang YM. Tetrahedron: Asymmetry 2006, 17: 330 - 223
Berkessel A.Guixa M.Schmidt F.Neudorfl JM.Lex J. Chem. Eur. J. 2007, 13: 4483 - 224
Aires-de-Sousa J.Prabhakar S.Lobo AM.Rosa AM.Gomes MJS.Corvo MC.Williams DJ.White AJP. Tetrahedron: Asymmetry 2002, 12: 3349 - 225
Murugan E.Siva A. Synthesis 2005, 2022 - 226
Fioravanti S.Mascia MG.Pellacani L.Tardella PA. Tetrahedron 2004, 60: 8073 - 227 For a review, see:
Pellissier H. Tetrahedron 2008, 64: 7041 -
228a
Papageorgiou CD.Ley SV.Gaunt MJ. Angew. Chem. Int. Ed. 2003, 42: 828 -
228b
Papageorgiou CD.Dios MACD.Ley SV.Gaunt MJ. Angew. Chem. Int. Ed. 2004, 43: 4641 -
229a
Bremeyer N.Smith SC.Ley SV.Gaunt MJ. Angew. Chem. Int. Ed. 2004, 43: 2681 -
229b
Johansson CCC.Bremeyer N.Ley SV.Owen DR.Smith SC.Gaunt MJ. Angew. Chem. Int. Ed. 2006, 45: 6024 - 230
Kojima S.Suzuki M.Watanabe A.Ohkata K. Tetrahedron Lett. 2006, 47: 9061 -
231a
Jew SS.Jeong BS.Yoo MS.Huh H.Park HG. Chem. Commun. 2001, 1244 -
231b
Park HG.Jeong BS.Yoo MS.Park MK.Huh H.Jew SS. Tetrahedron Lett. 2001, 42: 4645 -
231c
Park HG.Jeong BS.Yoo MS.Lee JH.Park MK.Lee YJ.Kim MJ.Jew SS. Angew. Chem. Int. Ed. 2002, 41: 3036 -
231d
Park HG.Jeong BS.Yoo MS.Lee JH.Park BS.Kim MG.Jew SS. Tetrahedron Lett. 2003, 44: 3497 -
231e
Lee JH.Yoo MS.Jung JH.Jew SS.Park HG.Jeong BS. Tetrahedron 2007, 63: 7906 -
232a
Jew SS.Yoo MS.Jeong BS.Park IY.Park HG. Org. Lett. 2002, 4: 4245 -
232b
Yoo MS.Jeong BS.Lee JH.Park HG.Jew SS. Org. Lett. 2005, 7: 1129 - 233
Andrus MB.Ye ZF.Zhang JQ. Tetrahedron Lett. 2005, 46: 3839 - 234
Lee YJ.Lee JY.Kim MJ.Kim TS.Park HG.Jew SS. Org. Lett. 2005, 7: 1557 - 235 For an account, see:
Lygo B.Beaumont DJ. Chimia 2007, 61: 257 -
236a
Lygo B.Crosby J.Lowdon TR.Wainwright PG. Tetrahedron 2001, 57: 2391 -
236b
Lygo B.Crosby J.Lowdon TR.Peterson JA.Wainwright PG. Tetrahedron 2001, 57: 2403 -
236c
Lygo B.Allbutt B. Synlett 2004, 326 -
236d
Lygo B.Andrews BI.Hirst JD.Melville JL.Peterson JA.Slack D. Chim. Oggi - Chem. Today 2004, 22: 8 -
237a
Lygo B.Crosby J.Peterson JA. Tetrahedron 2001, 57: 6447 -
237b
Lygo B.Humphreys LD. Tetrahedron Lett. 2002, 43: 6677 - 238
Lemaire C.Gillet S.Guillouet SP.Plenevaux A.Aerts JL.Luxen A. Eur. J. Org. Chem. 2004, 2899 - 239
Elango S.Venugopal M.Suresh PS. Tetrahedron 2005, 61: 1443 - 240
Kumar S.Ramachandran U. Tetrahedron 2005, 61: 7022 - 241
Li Q.Li L.Pei W.Wang S.Zhang Z. Synth. Commun. 2008, 38: 1470 - 242
Bozkurt S.Durmaz M.Yilmaz M.Sirit A. Tetrahedron: Asymmetry 2008, 19: 618 -
243a
Chinchilla R.Mazon P.Najera C. Tetrahedron: Asymmetry 2002, 13: 927 -
243b
Chinchilla R.Mazon P.Najera C.Ortega FJ. Tetrahedron: Asymmetry 2004, 15: 2603 -
244a
Siva A.Murugan E. Synthesis 2005, 2927 -
244b
Siva A.Murugan E. J. Mol. Catal. A: Chem. 2005, 241: 111 -
244c
Siva A.Murugan E. J. Mol. Catal. A: Chem. 2006, 248: 1 - 245
Chinchilla R.Najera C.Ortega FJ. Eur. J. Org. Chem. 2007, 6034 - 246
He W.Wang Q.Wang Q.Zhang B.Sun X.Zhang S. Synlett 2009, 1311 -
247a
Lv J.Zhang LP.Liu L.Wang YM. Chem. Lett. 2007, 36: 1354 -
247b
Wang X.Lv J.Liu L.Wang YM.Wu Y. J. Mol. Catal. A: Chem. 2007, 276: 102 - 248
Li L.Zhang ZP.Zhu XX.Popa A.Wang SW. Synlett 2005, 1873 - 249
Mase N.Ohno T.Morimoto H.Nitta F.Yoda H.Takabe K. Tetrahedron Lett. 2005, 46: 3213 -
250a
Thierry B.Perrard T.Audouard C.Plaquevent JC.Cahard D. Synthesis 2001, 1742 -
250b
Thierry B.Plaquevent JC.Cahard D. Tetrahedron: Asymmetry 2001, 12: 983 -
250c
Thierry B.Plaquevent JC.Cahard D. Tetrahedron: Asymmetry 2003, 14: 1671 - 251
Wang X.Yin L.Yang T.Wang YM. Tetrahedron: Asymmetry 2007, 18: 108 - 252
Danelli T.Annunziata R.Benaglia M.Cinquini M.Cozzi F.Tocco G. Tetrahedron: Asymmetry 2003, 14: 461 -
253a
Shi Q.Lee Y.Song H.Cheng M.Jew S.Park H.Jeong B. Chem. Lett. 2008, 37: 436 -
253b
Shi QH.Lee YJ.Kim MJ.Park NK.Lee KY.Song HR.Cheng MS.Jeong BS.Park HG.Jew SS. Tetrahedron Lett. 2008, 49: 1380 -
254a
Chinchilla R.Mazon P.Najera C. Adv. Synth. Catal. 2004, 346: 1186 -
254b
Chinchilla R.Mazon P.Najera C. Molecules 2004, 9: 349 - 255
Patterson DE.Xie SP.Jones LA.Osterhout MH.Henry CG.Roper TD. Org. Process Res. Dev. 2007, 11: 624 -
256a
Gong JH.Kim HR.Ryu EK.Kim JN. Bull. Korean Chem. Soc. 2002, 23: 789 -
256b
Kim J.-N.Lee H.-J.Lee K.-Y.Gong J.-H. Synlett 2002, 173 -
256c
Cho C.-W.Krische MJ. Angew. Chem. Int. Ed. 2004, 43: 6689 -
256d
Cho C.-W.Kong J.-R.Krische MJ. Org. Lett. 2004, 6: 1337 - 257
Kim J.-N.Lee H.-J.Gong J.-H. Tetrahedron Lett. 2002, 43: 9141 -
258a
Cui H.Feng X.Peng J.Lei J.Jiang K.Chen Y. Angew. Chem. Int. Ed. 2009, 48: 5737 -
258b
Feng X.Yuan Y.Cui H.Jiang K.Chen Y. Org. Biomol. Chem. 2009, 7: 3660 - 259
Du Y.Han X.Lu X. Tetrahedron Lett. 2004, 45: 4967 - 260
Van Steenis D.Marcelli T.Lutz M.Spek AL.Van Maarseveen JH.Hiemstra H. Adv. Synth. Catal. 2007, 349: 281 - 261
Jiang K.Peng J.Cui H.Chen Y. Chem. Commun. 2009, 3955 - 262
Ramachandran PV.Madhi S.Bland-Berry L.Reddy MVR.O’Donnell MJ. J. Am. Chem. Soc. 2005, 127: 13450 -
263a
Poulsen TB.Bernardi L.Bell M.Jørgensen KA. Angew. Chem. Int. Ed. 2006, 45: 6551 -
263b
Bell M.Poulsen TB.Jørgensen KA. J. Org. Chem. 2007, 72: 3053 -
263c
Poulsen T.Dickmeiss G.Overgaard J.Jørgensen K. Angew. Chem. Int. Ed. 2008, 47: 4687 -
264a
Bella M.Kobbelgaard S.Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 3670 -
264b
Kobbelgaard S.Bella M.Jørgensen KA. J. Org. Chem. 2006, 71: 4980 - For general reviews on asymmetric halogenations, see:
-
265a
Ueda M.Kano T.Maruoka K. Org. Biomol. Chem. 2009, 7: 2005 -
265b
France S.Weatherwax A.Lectka T. Eur. J. Org. Chem. 2005, 475 -
265c
Ibrahim H.Togni A. Chem. Commun. 2004, 1147 - For reviews on electrophilic fluorination, see:
-
266a
Ref. 70a.
-
266b
Shibata N.Ishimaru T.Nakamura S.Toru T.
J. Fluorine Chem. 2007, 128: 469 -
266c
Ref. 70d.
-
266d
Singh RP.Shreeve JM. Acc. Chem. Res. 2004, 37: 31 -
266e
Ref. 70e.
-
267a
Mohar B.Baudoux M.Plaquevent JC.Cahard D. Angew. Chem. Int. Ed. 2001, 40: 4214 -
267b
Mohar B.Sterk D.Ferron L.Cahard D. Tetrahedron Lett. 2005, 46: 5029 -
268a
Shibata N.Suzuki E.Asahi T.Shiro M. J. Am. Chem. Soc. 2001, 123: 7001 -
268b
Baudequin C.Plaquevent JC.Audouard C.Cahard D. Green Chem. 2002, 4: 584 -
268c
Baudequin C.Loubassou JF.Plaquevent JC.Cahard D. J. Fluorine Chem. 2003, 122: 189 -
268d
Thierry B.Audouard C.Plaquevent JC.Cahard D. Synlett 2004, 856 -
269a
Shibata N.Ishimaru T.Suzuki E.Kirk KL. J. Org. Chem. 2003, 68: 2494 -
269b
Zoute L.Audouard C.Plaquevent JC.Cahard D. Org. Biomol. Chem. 2003, 1: 1833 - 270
Greedy B.Paris JM.Vidal T.Gouverneur V. Angew. Chem. Int. Ed. 2003, 42: 3291 -
271a
Fukuzumi T.Shibata N.Sugiura M.Nakamura S.Toru T. J. Fluorine Chem. 2006, 127: 548 -
271b
Ishimaru T.Shibata N.Horikawa T.Yasuda N.Nakamura S.Toru T.Shiro M. Angew. Chem. Int. Ed. 2008, 47: 4157 -
272a
Kim DY.Park EJ. Org. Lett. 2002, 4: 545 -
272b
Park EJ.Kim HR.Joung CU.Kim DY. Bull. Korean Chem. Soc. 2004, 25: 1451 - 273
Bartoli G.Bosco M.Carlone A.Locatelli M.Melchiorre P.Sambri L. Angew. Chem. Int. Ed. 2005, 44: 6219 - 274
Pracejus H. Justus Liebigs Ann. Chem. 1960, 634: 9 -
275a
Gaunt MJ.Johansson CCC. Chem. Rev. 2007, 107: 5596 -
275b
Ref. 21a.
-
276a
France S.Wack H.Taggi AE.Hafez AM.Wagerle TR.Shah MH.Dusich CL.Lectka T. J. Am. Chem. Soc. 2004, 126: 4245 -
276b
France S.Bernstein D.Weatherwax A.Lectka T. Org. Lett. 2005, 7: 3009 -
276c
Dogo-Isonagie C.Bekele T.France S.Wolfer J.Weatherwax A.Taggi AE.Lectka T. J. Org. Chem. 2006, 71: 8946 -
276d
Dogo-Isonagie C.Bekele T.France S.Wolfer J.Weatherwax A.Taggi AE.Paull DH.Dudding T.Lectka T. Eur. J. Org. Chem. 2007, 1091 ; and references cited therein - For reviews, see:
-
277a
Atodiresei L.Schiffers I.Bolm C. Chem. Rev. 2007, 107: 5683 -
277b
Chen YG.Mcdaid P.Deng L. Chem. Rev. 2003, 103: 2965 -
277c
Spivey AC.Andrews BI. Angew. Chem. Int. Ed. 2001, 40: 3131 -
278a
Hiratake J.Yamamoto Y.Oda J. J. Chem. Soc., Chem. Commun. 1985, 1717 -
278b
Hiratake J.Inagaki M.Yamamoto Y.Oda J. J. Chem. Soc., Perkin Trans. 1 1987, 1053 -
279a
Aitken RA.Gopal J.Hirst JA. J. Chem. Soc., Chem. Commun. 1988, 632 -
279b
Aitken RA.Gopal J. Tetrahedron: Asymmetry 1990, 1: 517 -
280a
Bolm C.Gerlach A.Dinter C. Synlett 1999, 195 -
280b
Bolm C.Schiffers I.Dinter CL.Gerlach A. J. Org. Chem. 2000, 65: 6984 -
280c
Bolm C.Schiffers I.Dinter CL.Defrere L.Gerlach A.Raabe G. Synthesis 2001, 1719 -
280d
Bolm C.Atodiresei I.Schiffers I. Org. Synth. 2005, 82: 120 -
281a
Chen Y.Tian S.Deng L. J. Am. Chem. Soc. 2000, 122: 9542 -
281b
Choi C.Tian S.Deng L. Synthesis 2001, 1737 -
282a
Bolm C.Schiffers I.Atodiresei I.Hackenberger CPR. Tetrahedron: Asymmetry 2003, 14: 3455 -
282b
Rantanen T.Schiffers I.Bolm C. Org. Process Res. Dev. 2007, 11: 592 - 283
Yue TY.Mcleod DD.Albertson KB.Beck SR.Deerberg J.Fortunak JM.Nugent WA.Radesca LA.Tang LY.Xiang CD. Org. Process Res. Dev. 2006, 10: 262 - 284
Hameršak Z.Stipetic I.Avdagic A. Tetrahedron: Asymmetry 2007, 18: 1481 - 285
Mittendorf J.Benet-Buchholz J.Fey P.Mohrs KH. Synthesis 2003, 136 -
286a
Dai H.Chen W.Zhao L.Xiong F.Sheng H.Chen F. Adv. Synth. Catal. 2008, 350: 1635 -
286b
Huang J.Xiong F.Chen F. Tetrahedron: Asymmetry 2008, 19: 1436 - 287
Legrand F.Archambaud S.Collet S.Aphecetche-Julienne K.Guingant A.Evain M. Synlett 2008, 389 - 288
Ji L.Ma Y.Li J.Zhang L.Zhang L. Tetrahedron Lett. 2009, 50: 6166 - 289
Ishii Y.Fujimoto R.Mikami M.Murakami S.Miki Y.Furukawa Y. Org. Process Res. Dev. 2007, 11: 609 - 290
Ivšić T.Hameršak Z. Tetrahedron: Asymmetry 2009, 20: 1095 -
291a
Peschiulli A.Gun’ko Y.Connon S. J. Org. Chem. 2008, 73: 2454 -
291b
Peschiulli A.Quigley C.Tallon S.Gun’ko YK.Connon SJ. J. Org. Chem. 2008, 73: 6409 -
292a
Rho HS.Oh SH.Lee JW.Lee JY.Chin J.Song CE. Chem. Commun. 2008, 1208 -
292b
Oh SH.Rho H.Lee J.Lee J.Youk S.Chin J.Song C. Angew. Chem. Int. Ed. 2008, 47: 7872 - 293
Bigi F.Carloni S.Maggi R.Mazzacani A.Sartori G.Tanzi G. J. Mol. Catal. A: Chem. 2002, 182: 533 - 294
Wöltinger J.Krimmer HP.Drauz K. Tetrahedron Lett. 2002, 43: 8531 - 295
Kim HS.Song YM.Choi JS.Yang JW.Han H. Tetrahedron 2004, 60: 12051 -
296a
Chen YG.Deng L. J. Am. Chem. Soc. 2001, 123: 11302 -
296b
Hang JF.Tian SK.Tang L.Deng L. J. Am. Chem. Soc. 2001, 123: 12696 -
296c
Hang J.Deng L. Bioorg. Med. Chem. Lett. 2009, 19: 3856 -
297a
Tang L.Deng L. J. Am. Chem. Soc. 2002, 124: 2870 -
297b
Hang JF.Li HM.Deng L. Org. Lett. 2002, 4: 3321 -
297c
Hang JF.Deng L. Synlett 2003, 1927 - For reviews, see:
-
298a
Chenevert R.Pelchat N.Jacques F. Curr. Org. Chem. 2006, 10: 1067 -
298b
van Rantwijk F.Sheldon RA. Tetrahedron 2004, 60: 501 -
298c
Theil F. Catal. Today 1994, 22: 517 -
299a
Mizuta S.Sadamori M.Fujimoto T.Yamamoto I. Angew. Chem. Int. Ed. 2003, 42: 3383 -
299b
Mizuta S.Ohtsubo Y.Tsuzuki T.Fujimoto T.Yamamoto I. Tetrahedron Lett. 2006, 47: 8227 -
300a
Shibata N.Matsunaga M.Nakagawa M.Fukuzumi T.Nakamura S.Toru T. J. Am. Chem. Soc. 2005, 127: 1374 -
300b
Shibata N.Matsunaga M.Fukuzumi T.Nakamura S.Toru T. Synlett 2005, 1699 - 301
Peltier HM.Evans JW.Ellman JA. Org. Lett. 2005, 7: 1733 -
302a
Wynberg H.Staring EGJ. J. Am. Chem. Soc. 1982, 104: 166 -
302b
Wynberg H.Staring EGJ. J. Org. Chem. 1985, 50: 1977 -
303a
Calter MA. J. Org. Chem. 1996, 61: 8006 -
303b
Calter MA.Guo X. J. Org. Chem. 1998, 63: 5308 -
303c
Calter MA.Liao W.Struss JA. J. Org. Chem. 2001, 66: 7500 -
303d
Calter MA.Liao W. J. Am. Chem. Soc. 2002, 124: 13127 -
303e
Calter MA.Song W.Zhou JG. J. Org. Chem. 2004, 69: 1270 - 304
Calter MA.Orr RK.Song W. Org. Lett. 2003, 5: 4745 - 305
Armstrong A.Geldart SP.Jenner CR.Scutt JN.
J. Org. Chem. 2007, 72: 8091 -
306a
Cortez GS.Tennyson RL.Romo D. J. Am. Chem. Soc. 2001, 123: 7945 -
306b
Cortez GS.Oh SH.Romo D. Synthesis 2001, 1731 - 307
Calter MA.Tretyak OA.Flaschenriem C. Org. Lett. 2005, 7: 1809 - 308
Zhu C.Shen XQ.Nelson SG. J. Am. Chem. Soc. 2004, 126: 5352 - 309 For a review, see:
Fu N.Tidwell TT. Tetrahedron 2008, 64: 10465 -
310a
Taggi AE.Hafez AM.Wack H.Young B.Drury WJ.Lectka T. J. Am. Chem. Soc. 2000, 122: 7831 -
310b
Taggi AE.Hafez AM.Wack H.Young B.Ferraris D.Lectka T. J. Am. Chem. Soc. 2002, 124: 6626 -
310c
Shah MH.France S.Lectka T. Synlett 2003, 1937 -
310d
Hafez AM.Dudding T.Wagerle TR.Shah MH.Taggi AE.Lectka T. J. Org. Chem. 2003, 68: 5819 -
311a
France S.Wack H.Hafez AM.Taggi AE.Witsil DR.Lectka T. Org. Lett. 2002, 4: 1603 -
311b
France S.Shah MH.Weatherwax A.Wack H.Roth JP.Lectka T. J. Am. Chem. Soc. 2005, 127: 1206 - 312
Huang YZ.Calter MA. Tetrahedron Lett. 2007, 48: 1657 - 313
Zajac M.Peters R. Chem. Eur. J. 2009, 15: 8204 - For reviews, see:
-
314a
Shen J.Tan C. Org. Biomol. Chem. 2008, 6: 3229 -
314b
Kagan HB.Riant O. Chem. Rev. 1992, 92: 1007 -
315a
Riant O.Kagan HB. Tetrahedron Lett. 1989, 30: 7403 -
315b
Riant O.Kagan HB.Ricard L. Tetrahedron 1994, 50: 4543 - 316
Fache F.Piva O. Tetrahedron Lett. 2001, 42: 5655 -
317a
Bekele T.Shah MH.Wolfer J.Abraham CJ.Weatherwax A.Lectka T. J. Am. Chem. Soc. 2006, 128: 1810 -
317b
Wolfer J.Bekele T.Abraham CJ.Dogo-Isonagie C.Lectka T. Angew. Chem. Int. Ed. 2006, 45: 7398 -
317c
Paull D.Wolfer J.Grebinski JW.Weatherwax A.Lectka T. Chimia 2007, 61: 240 - 318
Abraham CJ.Paull DH.Bekele T.Scerba MT.Dudding T.Lectka T. J. Am. Chem. Soc. 2008, 130: 17085 - 319
Xu XA.Wang K.Nelson SG. J. Am. Chem. Soc. 2007, 129: 11690 - 320
Tiseni PS.Peters R. Angew. Chem. Int. Ed. 2007, 46: 5325 -
321a
Wang Y.Li HM.Wang YQ.Liu Y.Foxman BM.Deng L. J. Am. Chem. Soc. 2007, 129: 6364 -
321b
Singh RP.Bartelson K.Wang Y.Su H.Lu X.Deng L.
J. Am. Chem. Soc. 2008, 130: 2422 - 322
Waldmann H.Khedkar V.Dückert H.Schürmann M.Oppel IM.Kumar K. Angew. Chem. Int. Ed. 2008, 47: 6869 - 323
Alemparte C.Blay G.Jørgensen KA. Org. Lett. 2005, 7: 4569 - 324
Agbodjan A.Cooley B.Copley R.Corfield J.Flanagan R.Glover B.Guidetti R.Haigh D.Howes P.Jackson M.Matsuoka R.Medhurst K.Millar A.Sharp M.Slater M.Toczko J.Xie S. J. Org. Chem. 2008, 73: 3094 - 325
Xue M.Zhang X.Gong L. Synlett 2008, 691 -
326a
Guo C.Xue M.Zhu M.Gong L. Angew. Chem. Int. Ed. 2008, 47: 3414 -
326b
Xue M.Guo C.Gong L. Synlett 2009, 2191 - 327
Gioia C.Fini F.Mazzanti A.Bernardi L.Ricci A.
J. Am. Chem. Soc. 2009, 131: 9614 -
328a
Mues H.Kazmaier U. Synthesis 2001, 487 -
328b
Kazmaier U.Mues H.Krebs A. Chem. Eur. J. 2002, 8: 1850 -
329a
Pietrusiewicz KM.Koprowski M.Pakulski Z. Tetrahedron: Asymmetry 2002, 13: 1017 -
329b
Pakulski Z.Koprowski M.Pietrusiewicz KM. Tetrahedron 2003, 59: 8219 - 330
Dickmeiss G.De Sio V.Udmark J.Poulsen TB.Marcos V.Jørgensen KA. Angew. Chem. Int. Ed. 2009, 48: 6650 - 331
Wang M.Wang BM.Shi L.Tu YQ.Fan CA.Wang SH.Hu XD.Zhang SY. Chem. Commun. 2005, 5580 - 332
Kornblum N.DeLaMare HE. J. Am. Chem. Soc. 1951, 73: 880 - 333
Staben ST.Xin LH.Toste FD. J. Am. Chem. Soc. 2006, 128: 12658 - 334
Kobbelgaard S.Brandes S.Jørgensen KA. Chem. Eur. J. 2008, 14: 1464 -
335a
Overman LE. J. Am. Chem. Soc. 1974, 96: 597 -
335b
Overman LE. J. Am. Chem. Soc. 1976, 98: 2901 - 336
Çelebi-Ölçüm N.Aviyente V.Houk KN. J. Org. Chem. 2009, 74: 6944 - 337
Zhang E.Fan C.Tu Y.Zhang F.Song Y. J. Am. Chem. Soc. 2009, 131: 14626 - For recent reviews, see:
-
338a
Mohr JT.Hong AY.Stoltz BM. Nature Chem. 2009, 1: 359 -
338b
Blanchet J.Baudoux J.Amere M.Lasne M.Rouden J. Eur. J. Org. Chem. 2008, 5493 -
339a
Brunner H.Schmidt P. Eur. J. Org. Chem. 2000, 2119 -
339b
Brunner H.Schmidt P. Z. Naturforsch. 2000, 55b: 369 -
339c
Brunner H.Baur MA. Eur. J. Org. Chem. 2003, 2854 -
340a
Seitz T.Baudoux J.Bekolo H.Cahard D.Plaquevent JC.Lasne MC.Rouden J. Tetrahedron 2006, 62: 6155 -
340b
Amere M.Lasne MC.Rouden J. Org. Lett. 2007, 9: 2621 -
341a
Roy O.Diekmann M.Riahi A.Hénin F.Muzart J. Chem. Commun. 2001, 533 -
341b
Baur MA.Riahi A.Hénin F.Muzart J. Tetrahedron: Asymmetry 2003, 14: 2755 - 342
Kukula P.Matouscaronek V.Mallat T.Baiker A. Chem. Eur. J. 2008, 14: 2699 - 343
Blake AJ.Friend CL.Outram RJ.Simpkins NS.Whitehead AJ. Tetrahedron Lett. 2001, 42: 2877 -
344a
Andrus MB.Hicken EJ.Stephens JC. Org. Lett. 2004, 6: 2289 -
344b
Andrus MB.Hicken EJ.Stephens JC.Bedke DK. J. Org. Chem. 2005, 70: 9470 - 345
Andrus MB.Harper KC.Christiansen MA.Binkley MA. Tetrahedron Lett. 2009, 50: 4541 - 346
O’Donnell MJ.Cooper JT.Mader MM. J. Am. Chem. Soc. 2003, 125: 2370 -
347a
Acocella MR.Mancheno OG.Bella M.Jørgensen KA. J. Org. Chem. 2004, 69: 8165 -
347b
Sobhani S.Fielenbach D.Marigo M.Wabnitz TC.Jørgensen KA. Chem. Eur. J. 2005, 11: 5689 -
347c
Lopez-Cantarero J.Cid MB.Poulsen TB.Bella M.Ruano JLG.Jørgensen KA. J. Org. Chem. 2007, 72: 7062 - 348
Park EJ.Kim MH.Kim DY. J. Org. Chem. 2004, 69: 6897 - 349
Nibbs AE.Baize A.Herter RM.Scheidt KA. Org. Lett. 2009, 11: 4010 - 350
Moss TA.Fenwick DR.Dixon DJ. J. Am. Chem. Soc. 2008, 130: 10076 - 351
Wang Z.Sun X.Ye S.Wang W.Wang B.Wu J. Tetrahedron: Asymmetry 2008, 19: 964 - 352
Brozda D.Hoffman K.Rozwadowska MD. Heterocycles 2006, 67: 119 - 353
Frisch K.Jørgensen KA. Org. Biomol. Chem. 2007, 5: 2966 - 354
Kozio A.Furman B.Frelek J.WoŸnica M.Altieri E.Chmielewski M. J. Org. Chem. 2009, 74: 5687 - 355
Schmitt E.Schiffers I.Bolm C. Tetrahedron Lett. 2009, 50: 3185 - 356
Ku JM.Yoo MS.Park HG.Jew SS.Jeong BS. Tetrahedron 2007, 63: 8099 - 357
Sharma A.Sharma N.Kumar R.Sharma UK.Sinha AK. Chem. Commun. 2009, 5299 - 358
Cho DH.Jang DO. Chem. Commun. 2006, 5045 - 359
Poisson T.Dalla V.Marsais F.Dupas G.Oudeyer S.Levacher V. Angew. Chem. Int. Ed. 2007, 46: 7090 - 360
Hintermann L.Schmitz M. Adv. Synth. Catal. 2008, 350: 1469
References
In simpler words: if both quinine and quinidine lacked the C3-vinyl groups, they would be enantiomers.
6Prices from the Sigma-Aldrich website (November 2009, Italy): quinine, 50 g - ı 131.30; quinidine, 50 g - ı 288 40; cinchonidine, 100 g - ı 111.10; cinchonine, 100 g - ı 115.20