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DOI: 10.1055/s-0030-1260022
TADDOL-Derived Phosphonites, Phosphites, and Phosphoramidites in Asymmetric Catalysis
Publication History
Publication Date:
10 May 2011 (online)
Abstract
In metal-based asymmetric catalysis, desirable attributes for chiral ligands include low cost, simplicity of synthesis, and ease of variation to enable fine-tuning of a particular transformation. TADDOL-derived phosphonites, phosphites, and phosphoramidites constitute one family of chiral ligand that possesses these features. In recent times, these ligands have excelled in a wide range of catalytic asymmetric reactions. This review article summarizes progress in this area.
1 Introduction
2 Synthesis of TADDOL-Derived Phosphorus Ligands
3 Hydrosilylations
4 Hydroborations and Diborations
5 Hydrogenations
6 Conjugate Additions
7 Allylic Substitutions
8 Nucleophilic Allylations
9 Cycloadditions
10 Miscellaneous Reactions
11 Conclusion
Key words
asymmetric catalysis - phosphorus - ligands - enantioselectivity - TADDOL
-
1a
Catalytic Asymmetric Synthesis
3rd
ed.:
Ojima I. John Wiley & Sons, Inc.; Hoboken: 2010. -
1b
Asymmetric Catalysis
on Industrial Scale: Challenges, Approaches and Solutions
Blaser H.-U.Schmidt E. Wiley-VCH; Weinheim: 2004. -
1c
Comprehensive
Asymmetric Catalysis
Vols. I-III:
Jacobsen EN.Pfaltz A.Yamamoto H. Springer; Berlin: 1999. - 2
Bredig G.Fiske PS. Biochem. Z. 1913, 46: 7 - For selected early contributions, see:
-
3a
Akabori S.Sakurai S.Izumi Y.Fujii Y. Nature 1956, 178: 323 -
3b
Knowles WS.Sabacky MJ. Chem. Commun. 1968, 1445 -
3c
Dang TP.Kagan HB. J. Chem. Soc. D, Chem. Commun. 1971, 481 -
3d
Knowles WS.Sabacky MJ.Vineyard BD. J. Chem. Soc., Chem. Commun. 1972, 10 -
3e
Kagan HB.Dang TP. J. Am. Chem. Soc. 1972, 94: 6429 -
3f
Vineyard BD.Knowles WS.Sabacky MJ.Bachman GL.Weinkauff DJ. J. Am. Chem. Soc. 1977, 99: 5946 -
4a Organocatalysis
special feature: Proc. Natl. Acad. Sci. U.S.A.
2010,
107:
20618
-
4b
Macmillan DWC. Nature 2008, 455: 304 -
4c
Dondoni A.Massi A. Angew. Chem. Int. Ed. 2008, 47: 4638 -
4d Special issue for organocatalysis: Chem.
Rev.
2007,
107:
5413; List,
B. (guest editor)
-
4e
Enantioselective
Organocatalysis: Reactions and Experimental Procedures
Dalko PI. Wiley-VCH; Weinheim: 2007. -
4f
Gaunt MJ.Johansson CCC.McNally A.Vo NT. Drug Discovery Today 2007, 12: 8 -
4g
Berkessel A.Gröger H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis Wiley-VCH; Weinheim: 2005. - 5
Phosphorus Ligands in Asymmetric
Catalysis: Synthesis and Applications
Börner A. Wiley-VCH; Weinheim: 2010. - 6
Seebach D.Beck AK.Heckel A. Angew. Chem. Int. Ed. 2001, 40: 92 - 7
Seebach D.Beck AK.Imwinkelried R.Roggo S.Wonnacott A. Helv. Chim. Acta 1987, 70: 954 - 8
Seebach D.Hayakawa M.Sakaki J.Schweizer WB. Tetrahedron 1993, 49: 1711 - 9
Sakaki J.Schweizer WB.Seebach D. Helv. Chim. Acta 1993, 76: 2654 - 10
Yoon TP.Jacobsen EN. Science 2003, 299: 1691 - 11
Pellissier H. Tetrahedron 2008, 64: 10279 - 12
Bruneau C.Renaud J.-L. In Phosphorus Ligands in Asymmetric Catalysis Vol. 1 :Börner A. Wiley-VCH; Weinheim: 2008. p.36 - 13
Ansell J.Wills M. Chem. Soc. Rev. 2002, 31: 259 - 14
van Leeuwen PWNM.Kamer PCJ.Claver C.Pàmies O.Diéguez M. Chem. Rev. 2011, 111: 2077 -
15a Chiral
phosphoramidites in asymmetric conjugate addition:
Feringa BL. Acc. Chem. Res. 2000, 33: 346 -
15b Chiral phosphoramidites
in asymmetric hydrogenation:
Minnaard AJ.Feringa BL.Lefort L.de Vries JG. Acc. Chem. Res. 2007, 40: 1267 -
15c Chiral phosphoramidite
review:
Teichert JF.Feringa BL. Angew. Chem. Int. Ed. 2010, 49: 2486 - 16
Sieber JD.Liu S.Morken JP. J. Am. Chem. Soc. 2007, 129: 2214 -
17a
Morgan JB.Miller SP.Morken JP. J. Am. Chem. Soc. 2003, 125: 8702 -
17b
Trudeau S.Morgan JB.Shrestha M.Morken JP. J. Org. Chem. 2005, 70: 9538 -
17c See also:
Ramírez J.Segarra AM.Fernández E. Tetrahedron: Asymmetry 2005, 16: 1289 - 18
Alexakis A.Burton J.Vastra J.Benhaim C.Fournioux X.van den Heuvel A.Levêque J.-M.Mazé F.Rosset S. Eur. J. Org. Chem. 2000, 4011 - 19
Mewald M.Weickgenannt A.Fröhlich R.Oestreich M. Tetrahedron: Asymmetry 2010, 21: 1232 - 20
Yao S.Meng J.-C.Siuzdak G.Finn MG. J. Org. Chem. 2003, 68: 2540 - 21
Smith SM.Thacker NC.Takacs JM. J. Am. Chem. Soc. 2008, 130: 3734 - 22
Smith SM.Takacs JM. J. Am. Chem. Soc. 2010, 132: 1740 - 23
Mandoli A.Arnold LA.de Vries AHM.Salvadori P.Feringa BL. Tetrahedron: Asymmetry 2001, 12: 1929 - 24
Boele MDK.Kamer PCJ.Lutz M.Spek AL.de Vries JG.van Leeuwen PWNM.van Strijdonck GPF. Chem. Eur. J. 2004, 10: 6232 - 25
Woodward AR.Burks HE.Chan LM.Morken JP. Org. Lett. 2005, 7: 5505 - 26
Moteki SA.Wu D.Chandra KL.Reddy DS.Takacs JM. Org. Lett. 2006, 8: 3097 - 27
Yu RT.Rovis T. J. Am. Chem. Soc. 2006, 128: 12370 - 28
Palacios F.Vicario J. Org. Lett. 2006, 8: 5405 - 29
Burks HE.Liu S.Morken JP. J. Am. Chem. Soc. 2007, 129: 8766 - 30
Lee E.Rovis T. Org. Lett. 2008, 10: 1231 - 31
Yu R.Rovis T. J. Am. Chem. Soc. 2008, 130: 3262 - 32
Dalton DM.Oberg KM.Yu RT.Lee EE.Perreault S.Oinen ME.Pease ML.Malik G.Rovis T. J. Am. Chem. Soc. 2009, 131: 15717 - 33
Yu RT.Friedman RK.Rovis T. J. Am. Chem. Soc. 2009, 131: 13250 - 34
Albicker MR.Cramer N. Angew. Chem. Int. Ed. 2009, 48: 9139 - 35
Wassenaar J.de Bruin B.Reek JNH. Organometallics 2010, 29: 2767 - 36
Mariz R.Briceño A.Dorta R.Dorta R. Organometallics 2008, 27: 6605 - 37
Shirakura M.Suginome M. Angew. Chem. Int. Ed. 2010, 49: 3827 - 38
Teller H.Flügge S.Goddard R.Fürstner A. Angew. Chem. Int. Ed. 2010, 49: 1949 - 39
Heldmann DK.Seebach D. Helv. Chim. Acta 1999, 82: 1096 -
40a
Guo J.Wu J.Siuzdak G.Finn M. Angew. Chem. Int. Ed. 1999, 38: 1755 -
40b
Díaz DD.Yao S.Finn M. Tetrahedron Lett. 2001, 42: 2617 - 41
Kranich R.Eis K.Geis O.Mühle S.Bats JW.Schmalz H.-G. Chem. Eur. J. 2000, 6: 2874 - 42
Blume F.Zemolka S.Fey T.Kranich R.Schmalz H.-G. Adv. Synth. Catal. 2002, 344: 868 - 43
Werle S.Fey T.Neudörfl JM.Schmalz H.-G. Org. Lett. 2007, 9: 3555 ; Additions and corrections: Org. Lett. 2007, 9, 4085 - 44
Takacs JM.Reddy DS.Moteki SA.Wu D.Palencia H. J. Am. Chem. Soc. 2004, 126: 4494 - 45
Moteki SA.Takacs JM. Angew. Chem. Int. Ed. 2008, 47: 894 - 46
Carroll A.-M.O’Sullivan TP.Guiry PJ. Adv. Synth. Catal. 2005, 347: 609 - 47 For a review of substrate-directable
chemical reactions, see:
Hoveyda AH.Evans DA.Fu GC. Chem. Rev. 1993, 93: 1307 -
48a
Evans DA.Fu GC. J. Am. Chem. Soc. 1991, 113: 4042 -
48b
Evans DA.Fu GC.Hoveyda AH. J. Am. Chem. Soc. 1992, 114: 6671 - 49
Smith SM.Takacs J. Org. Lett. 2010, 12: 4612 -
50a
Ishiyama T.Kitano T.Miyaura N. Tetrahedron Lett. 1998, 39: 2357 -
50b
Yang F.-Y.Cheng C.-H. J. Am. Chem. Soc. 2001, 123: 761 - 51
Pelz NF.Woodward AR.Burks HE.Sieber JD.Morken JP. J. Am. Chem. Soc. 2004, 126: 16328 - 52
Pelz NF.Morken JP. Org. Lett. 2006, 8: 4557 - 53
Sieber JD.Morken JP. J. Am. Chem. Soc. 2006, 128: 74 - 54
Kliman LT.Mlynarski SN.Morken JP. J. Am. Chem. Soc. 2009, 131: 13210 - 55
Burks HE.Kliman LT.Morken JP. J. Am. Chem. Soc. 2009, 131: 9134 - 56
Hilgraf R.Pfaltz A. Synlett 1999, 1814 - 57
Wassenaar J.Reek JNH. J. Org. Chem. 2009, 74: 8403 - For general reviews covering metal-catalyzed enantioselective conjugate additions, see:
-
58a
Catalytic Asymmetric
Conjugate Reactions
Córdova A. Wiley-VCH; Weinheim: 2010. -
58b
Christoffers J.Koripelly G.Rosiak A.Rössle M. Synthesis 2007, 1279 -
58c
Krause N.Hoffmann-Röder A. Synthesis 2001, 171 -
59a
Jerphagnon T.Pizzuti MG.Minnaard AJ.Feringa BL. Chem. Soc. Rev. 2009, 38: 1039 -
59b
Thaler T.Knochel P. Angew. Chem. Int. Ed. 2009, 48: 645 -
59c
Harutyunyan SR.den Hartog T.Geurts K.Minnaard AJ.Feringa BL. Chem. Rev. 2008, 108: 2824 -
59d
Alexakis A.Bäckvall JE.Krause N.Pàmies O.Diéguez M. Chem. Rev. 2008, 108: 2796 -
59e
Lopez F.Minnaard AJ.Feringa BL. Acc. Chem. Res. 2007, 40: 179 -
59f
Alexakis A.Benhaim C. Eur. J. Org. Chem. 2002, 3221 - For reviews covering rhodium-catalyzed conjugate addition of organometallic reagents, see:
-
60a
Edwards HJ.Hargrave JD.Penrose SD.Frost CG. Chem. Soc. Rev. 2010, 39: 2093 -
60b
Yoshida K.Hayashi T. In Modern Rhodium-Catalyzed Organic ReactionsEvans PA. Wiley-VCH; Weinheim: 2005. Chap. 3. p.55 -
60c
Hayashi T. Bull. Chem. Soc. Jpn. 2004, 77: 13 -
60d
Hayashi T.Yamasaki K. Chem. Rev. 2003, 103: 2829 -
61a
Alexakis A.Mutti S.Normant JF. J. Am. Chem. Soc. 1991, 113: 6332 -
61b
Alexakis A.Frutos J.Manganey P. Tetrahedron: Asymmetry 1993, 4: 2427 -
62a
de Vries AHM.Meetsma A.Feringa BL. Angew. Chem., Int. Ed. Engl. 1996, 35: 2374 -
62b
Feringa BL.Pineschi M.Arnold LA.Imbos R.de Vries AHM. Angew. Chem., Int. Ed. Engl. 1997, 36: 2620 - 63 For a preliminary account of the
work in ref. 18, see:
Alexakis A.Vastra J.Burton J.Benhaim C.Manganey P. Tetrahedron Lett. 1998, 39: 7869 - 64
Keller E.Maurer J.Naasz R.Schader T.Meetsma A.Feringa BL. Tetrahedron: Asymmetry 1998, 9: 2409 - 65
Alexakis A.Benhaïm C.Fournioux X.van den Heuvel A.Levêque J.-M.March S.Rosset S. Synlett 1999, 1811 - 66
Vuagnoux-d’Augustin M.Alexakis A. Eur. J. Org. Chem. 2007, 5852 - For reviews of nitroalkenes as conjugate acceptors, see:
-
67a
Seebach D.Colvin EW.Lehr F.Weller T. Chimia 1979, 33: 1 -
67b
Barrett AGM.Graboski GG. Chem. Rev. 1986, 86: 751 -
67c
Barrett AGM. Chem. Soc. Rev. 1991, 20: 95 -
67d
Berner OM.Tedeschi L.Enders D. Eur. J. Org. Chem. 2002, 12: 1877 - 68
Alexakis A.Vastra J.Manganey P. Tetrahedron Lett. 1997, 38: 7745 - 69 For magnesium- and titanium-catalyzed
addition of dialkylzinc reagents to nitroalkenes, see:
Schäfer H.Seebach D. Tetrahedron 1995, 51: 2305 - 70
Alexakis A.Benhaim C. Org. Lett. 2000, 2: 2579 - 71
Duursma A.Minnaard AJ.Feringa BL. Tetrahedron 2002, 58: 5773 - 72
Sewald N.Wendisch V. Tetrahedron: Asymmetry 1998, 9: 1341 - 73
Versleijen JPG.van Leusen AM.Feringa BL. Tetrahedron Lett. 1999, 40: 5803 - 74
Duursma A.Minnaard AJ.Feringa BL. J. Am. Chem. Soc. 2003, 125: 3700 - 75
Alexakis A.Polet D.Benhaim C.Rosset S. Tetrahedron: Asymmetry 2004, 15: 2199 - 76
Choi H.Hua Z.Ojima I. Org. Lett. 2004, 6: 2689 - 77
Wakabayashi K.Aikawa K.Kawauchi S.Mikami K.
J. Am. Chem. Soc. 2008, 130: 5012 -
78a
Luchaco-Cullis CA.Hoveyda AH. J. Am. Chem. Soc. 2002, 124: 8192 -
78b
Mampreian DM.Hoveyda AH. Org. Lett. 2004, 6: 2829 -
78c
Wu J.Mampreian DM.Hoveyda AH. J. Am. Chem. Soc. 2005, 127: 4584 - 79
Alexakis A.Benhaim C. Tetrahedron: Asymmetry 2001, 12: 1151 - 80
Schuppan J.Minnaard AJ.Feringa BL. Chem. Commun. 2004, 792 - 81
Watanabe T.Knopfel TF.Carreira EM. Org. Lett. 2003, 5: 4557 - 82
Fillion E.Wilsily A. J. Am. Chem. Soc. 2006, 128: 2774 - 83
Palacios F.Vicario J. Synthesis 2007, 3923 -
84a
Trost BM.Van Vranken DL. Chem. Rev. 1996, 96: 395 -
84b
Trost BM.Crawley ML. Chem. Rev. 2003, 103: 2921 - 85
Alexakis A.Malan C.Lea L.Benhaim C.Fournioux X. Synlett 2001, 927 - 86
Alexakis A.Croset K. Org. Lett. 2002, 4: 4147 - 87
Bertozzi F.Crotti P.Macchia F.Pineschi M.Arnold A.Feringa BL. Tetrahedron Lett. 1999, 40: 4893 -
88a
Prétôt R.Pfaltz A. Angew. Chem. Int. Ed. 1998, 37: 323 -
88b
Prétot R.Lloyd-Jones GC.Pfaltz A. Pure Appl. Chem. 1998, 70: 1035 - 89
Bronger RPJ.Guiry PJ. Tetrahedron: Asymmetry 2007, 18: 1094 - 90
Mikhel IS.Bernardinelli G.Alexakis A. Inorg. Chim. Acta 2006, 359: 1826 - 91
Takacs JM.Reddy DS.Moteki SA.Wu D.Palencia H. J. Am. Chem. Soc. 2004, 126: 4494 - For selected reviews, see:
-
92a
Denmark SE.Fu J. Chem. Rev. 2003, 103: 2763 -
92b
Kanai M.Wada R.Shibuguchi T.Shibasaki M. Pure Appl. Chem. 2008, 80: 1055 -
92c
Han SB.Kim IS.Krische MJ. Chem. Commun. 2009, 47: 7278 - 93
Sieber JD.Morken JP. J. Am. Chem. Soc. 2008, 130: 4978 -
94a
Morita M.Inoue K.Ogoshi S.Kurosawa H. Organometallics 2003, 22: 5468 -
94b
Ogoshi S.Yoshida T.Nishida T.Morita M.Kurosawa H. J. Am. Chem. Soc. 2001, 123: 1944 -
94c
Ogoshi S.Tomiyasu S.Morita M.Kurosawa H. J. Am. Chem. Soc. 2002, 124: 11598 -
95a
Johnson JR.Tully PS.Mackenzie PB.Sabat M. J. Am. Chem. Soc. 1991, 113: 6172 -
95b
Grisso BA.Johnson JR.Mackenzie PB. J. Am. Chem. Soc. 1992, 114: 5160 -
96a
Méndez M.Cuerva JM.Gómez-Bengoa E.Cárdenas DJ.Echavarren AM. Chem. Eur. J. 2002, 8: 3620 -
96b
Cárdenas DJ.Echavarren AM. New J. Chem. 2004, 28: 338 -
96c
Ariafard A.Lin Z. J. Am. Chem. Soc. 2006, 128: 13010 - 97
Zhang P.Morken JP. J. Am. Chem. Soc. 2009, 131: 12550 - 98
Wallner OA.Olsson VJ.Eriksson L.Szabó MJ. Inorg. Chim. Acta 2006, 359: 1767 - 99
Yu RT.Rovis T. J. Am. Chem. Soc. 2006, 128: 2782 - For examples of CO migration from rhodium(III) species, see:
-
100a
Cavallo L.Sola M. J. Am. Chem. Soc. 2001, 123: 12294 -
100b
Gonsalvi L.Adams H.Sunley GJ.Ditzel E.Haynes A. J. Am. Chem. Soc. 2002, 124: 13597 -
100c
Gonsalvi L. Organometallics 2003, 22: 1047 - For selected reviews, see:
-
101a
Li Z.Brouwer C.He C. Chem. Rev. 2008, 108: 3239 -
101b
Arcadi A. Chem. Rev. 2008, 108: 3266 -
101c
Jiménez-Núnez E.Echavarren AM. Chem. Rev. 2008, 108: 3326 -
101d
Fürstner A.Davies PW. Angew. Chem. Int. Ed. 2007, 46: 3410 -
101e
Gorin DJ.Toste FD. Nature 2007, 446: 395 -
101f
Hashmi ASK. Chem. Rev. 2007, 107: 3180 - 102
Johnson JB.Bercot EA.Williams CM.Rovis T. Angew. Chem. Int. Ed. 2007, 46: 4514 - 103
Johnson JB.Cook MJ.Rovis T. Tetrahedron 2009, 65: 3202 - For enantioselective ring-opening of meso and prochiral cyclic anhydrides into isopropyl hemiesters using stoichiometric diisopropxytitanium TADDOLates, see:
-
104a
Seebach D.Jaeschke G.Wang YM. Angew. Chem., Int. Ed. Engl. 1995, 34: 2395 -
104b
Seebach D.Jaeschke G. J. Org. Chem. 1998, 63: 1190 -
105a
Bercot EA.Rovis T. J. Am. Chem. Soc. 2002, 124: 174 -
105b
Bercot EA.Rovis T. J. Am. Chem. Soc. 2005, 127: 247 -
105c
Johnson JB.Bercot EA.Rowley JM.Coates GW.Rovis T. J. Am. Chem. Soc. 2007, 129: 2718 -
105d
Johnson JB.Yu RT.Fink P.Bercot EA.Rovis T. Org. Lett. 2006, 8: 4307 -
105e
Rogers RL.Moore JL.Rovis T. Angew. Chem. Int. Ed. 2007, 46: 9301 - 106
Bercot EA.Rovis T. J. Am. Chem. Soc. 2004, 126: 10248 - 107
Cook MJ.Rovis T. J. Am. Chem. Soc. 2007, 129: 9302 -
108a
Carroll AR.Taylor WC. Aust. J. Chem. 1991, 44: 1615 -
108b
Carroll AR.Taylor WC. Aust. J. Chem. 1991, 44: 1705 - For recent selected reviews, see:
-
109a
Mkhalid IAI.Barnard JH.Marder TB.Murphy JM.Hartwig JF. Chem. Rev. 2010, 110: 890 -
109b
Chen X.Engle KM.Wang D.-H.Yu J.-Q. Angew. Chem. Int. Ed. 2009, 48: 5094 -
109c
Thansandote P.Lautens M. Chem. Eur. J. 2009, 15: 5874 -
109d
Joucla L.Djakovitch L. Adv. Synth. Catal. 2009, 351: 673 -
109e
Daugulis O.Do H.-Q.Shabashov C. Acc. Chem. Res. 2009, 42: 1074 -
109f
Alberico D.Scott ME.Lautens M. Chem. Rev. 2007, 107: 174 -
110a
Shi B.-F.Maugel N.Zhang Z.-H.Yu J.-Q. Angew. Chem. Int. Ed. 2008, 47: 4882 -
110b
Shi B.-F.Zhang Y.-H.Lam JK.Wang D.-H.Yu J.-Q. J. Am. Chem. Soc. 2010, 132: 460 - 111
Peng HM.Dai L.-X.You S.-L. Angew. Chem. Int. Ed. 2010, 49: 5826 - 112 For a review of diastereoselective
and enantioselective transition-metal-catalyzed C-H activation
reactions, see:
Giri R.Shi B.-F.Engle KM.Maugel N.Yu J.-Q. Chem. Soc. Rev. 2009, 38: 3242 -
113a
Thalji RK.Ellman JA.Bergman RG. J. Am. Chem. Soc. 2004, 126: 7192 -
113b
Harada H.Thalji RK.Bergman RG.Ellman JA. J. Org. Chem. 2008, 73: 6772 -
114a
Thalji RK.Ahrendt KA.Ellman JA.Bergman RG. J. Am. Chem. Soc. 2001, 123: 9692 -
114b
Ahrendt KA.Bergman RG.Ellman JA. Org. Lett. 2003, 5: 1301 -
115a
Imbos R.Minnaard AJ.Feringa BL. J. Am. Chem. Soc. 2002, 124: 184 -
115b
Imbos R.Minnaard AJ.Feringa BL. Dalton Trans. 2003, 2017 - 116
Waibel M.Cramer N. Angew. Chem. Int. Ed. 2010, 49: 4455 - 117
Robert T.Abiri Z.Wassenaar J.Sandee AJ.Romanski S.Neudörfl J.-M.Schmalz H.-G.Reek JNH. Organometallics 2010, 29: 478 - 118 For a seminal reference, see:
Revis A.Hilty TK. Tetrahedron Lett. 1987, 28: 4809 - For reviews, see:
-
119a
Han SB.Hassan A.Krische MJ. Synthesis 2008, 2669 -
119b
Garner S.Han SB.Krische MJ. In Modern ReductionsAndersson P.Munslow I. Wiley-VCH; Weinheim: 2008. p.387 -
119c
Nishiyama H.Shiomi T. Top. Curr. Chem. 2007, 279: 105 -
119d
Jang H.-Y.Krische MJ. Eur. J. Org. Chem. 2004, 3953 -
119e
Jang H.-Y.Krische MJ. Acc. Chem. Res. 2004, 37: 653 -
119f
Huddleston RR.Krische MJ. Synlett 2003, 12 -
119g
Chiu P. Synthesis 2004, 2210 -
119h
Motherwell WB. Pure Appl. Chem. 2002, 74: 135 -
120a
Jang HY.Huddleston RR.Krische MJ. J. Am. Chem. Soc. 2002, 124: 15156 -
120b
Huddleston RR.Krische MJ. Org. Lett. 2003, 5: 1143 -
120c
Koech PK.Krische MJ. Org. Lett. 2004, 6: 691 -
120d
Marriner GA.Garner SA.Jang HY.Krische MJ. J. Org. Chem. 2004, 69: 1380 -
120e
Jung CK.Garner SA.Krische MJ. Org. Lett. 2006, 8: 519 -
120f
Han SB.Krische MJ. Org. Lett. 2006, 8: 5657 -
120g
Jung CK.Krische MJ. J. Am. Chem. Soc. 2006, 128: 17051 - 121
Bee C.Han SB.Hassan A.Iida H.Krische MJ.
J. Am. Chem. Soc. 2008, 130: 2746 -
122a
Shirakura M.Suginome M. J. Am. Chem. Soc. 2008, 130: 5410 -
122b
Shirakura M.Suginome M. Org. Lett. 2009, 11: 523 -
122c
Shirakura M.Suginome M. J. Am. Chem. Soc. 2009, 131: 5060 - 123
Müller P.Nury P. Helv. Chim. Acta 2001, 84: 662 - 124
Weickgenannt A.Mewald M.Muesmann TWT.Oestreich M. Angew. Chem. Int. Ed. 2010, 49: 2223 -
125a
Rendler S.Auer G.Oestreich M. Angew. Chem. Int. Ed. 2005, 44: 7620 -
125b
Klare HFT.Oestreich M. Angew. Chem. Int. Ed. 2007, 46: 9335 -
125c
Rendler S.Plefka O.Karatas B.Auer G.Fröhlich R.MückLichtenfeld C.Grimme S.Oestreich M. Chem. Eur. J. 2008, 14: 11512 -
125d
Karatas B.Rendler S.Fröhlich R.Oestreich M. Org. Biomol. Chem. 2008, 6: 1435 -
125e
Steves A.Oestreich M. Org. Biomol. Chem. 2009, 7: 4464