Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(16): 2679-2702
DOI: 10.1055/s-0030-1258164
DOI: 10.1055/s-0030-1258164
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
Alternative Synthetic Strategies for Enantioselective Construction of Halogenated Chiral Carbon Centers
Further Information
Received
14 March 2010
Publication Date:
07 July 2010 (online)
Publication History
Publication Date:
07 July 2010 (online)
Abstract
This review focuses on the enantioselective synthesis of halogenated molecules having a chiral halocarbon center. In particular, this review discusses enantioselective transformations with haloalkenes and enantioselective α-substitutions of α-halo carbonyl compounds. Enantioselective halogen-transfer reactions are excluded from this review.
1 Introduction
2 Enantioselective Transformations with Halogenated Alkenes
2.1 Diels-Alder Reactions
2.2 Cyclopropanations
2.3 Hydrogenations and Epoxidations
2.4 Conjugate Additions to Halogenated Alkenes and Miscellaneous Reactions
3 Enantioselective α-Functionalizations of α-Halo Carbonyl Compounds or Their Enolates
3.1 Aldol-type Reactions
3.2 Alkylations with Phase-Transfer Catalysts and Allylations with Palladium Catalysts
3.3 Conjugate Additions of α-Halo Carbonyl Compounds
3.4 Heterofunctionalizations and Protonations
4 Conclusions
Key words
halogens - fluorine - asymmetric synthesis - asymmetric catalysis - alkyl halides
-
1a
Fluorine in medicinal chemistry and chemical
biology
Ojima I. Wiley & Sons; New York: 2009. -
1b
Bégué J.-P.Bonnet-Delphon D. Bioorganic and Medicinal Chemistry of Fluorine Wiley & Sons; Hoboken: 2008. - 2 For a review on enantioselective
construction of fluorinated chiral carbon centers, see:
Prakash GKS.Beier P. Angew. Chem. Int. Ed. 2006, 45: 2172 - 3 For a review on catalytic asymmetric
reactions with fluorinated carbonyl and olefinic compounds, see:
Mikami K.Itoh Y.Yamanaka M. Chem. Rev. 2004, 104: 1 - For reviews focused on the asymmetric fluorination, see:
-
4a
Brunet VA.O’Hagan D. Angew. Chem. Int. Ed. 2008, 47: 1179 -
4b
Shibata N.Ishimaru T.Nakamura S.Toru T. J. Fluorine Chem. 2007, 128: 469 -
4c
Pihko PM. Angew. Chem. Int. Ed. 2006, 45: 544 -
4d
Bobbio C.Gouverneur V. Org. Biomol. Chem. 2006, 4: 2065 -
4e
Ma J.-A.Cahard D. Chem. Rev. 2004, 104: 6119 -
4f
Ma J.-A.Cahard D. Chem. Rev. 2008, 108: PR1-PR43 -
4g
Muñiz K. Angew. Chem. Int. Ed. 2001, 40: 1653 - For reviews focused on the asymmetric halogenation, see:
-
5a
Ueda M.Kano T.Maruoka K. Org. Biomol. Chem. 2009, 7: 2005 -
5b
Hamashima Y.Sodeoka M. Synlett 2006, 1467 -
5c
Marigo M.Jørgensen KA. Chem. Commun. 2006, 2001 -
5d
Oestreich M. Angew. Chem. Int. Ed. 2005, 44: 2324 -
5e
France S.Weatherwax A.Lectka T. Eur. J. Org. Chem. 2005, 475 -
5f
Ibrahim H.Togni A. Chem. Commun. 2004, 1147 -
6a
Acid Catalysis in Modern Organic Synthesis
Yamamoto H.Ishihara K. Wiley-VCH; Weinheim: 2008. -
6b
Lewis
Acids in Organic Synthesis
Yamamoto H. Wiley-VCH; Weinheim: 2000. -
6c
Evans DA.Johnson JS. In Comprehensive Asymmetric Catalysis Vol. III:Jacobsen E.Pfaltz A.Yamamoto H. Springer-Verlag; Berlin: 1999. p.1177 - 8
Ishihara K.Gao Q.Yamamoto H. J. Org. Chem. 1993, 58: 6917 - 9
Corey EJ.Loh T.-P. J. Am. Chem. Soc. 1991, 113: 8966 -
10a
Corey EJ.Weinschenker NM.Schaaf TK.Huber W. J. Am. Chem. Soc. 1969, 91: 5675 -
10b
Corey EJ.Schaaf TK.Huber W.Koelliker U.Weinschenker NM. J. Am. Chem. Soc. 1970, 92: 397 - 11
Corey EJ.Guzman-Perez A.Loh T.-P. J. Am. Chem. Soc. 1994, 116: 3611 - 12
Corey EJ.Loh T.-P. Tetrahedron Lett. 1993, 34: 3979 - 13
Schindler CS.Stephenson CRJ.Carreira EM. Angew. Chem. Int. Ed. 2008, 47: 8852 - 14
Hayashi Y.Rohde JJ.Corey EJ. J. Am. Chem. Soc. 1996, 118: 5502 -
15a
Ishihara K.Yamamoto H. J. Am. Chem. Soc. 1994, 116: 1561 -
15b
Ishihara K.Kurihara H.Yamamoto H. J. Am. Chem. Soc. 1996, 118: 3049 -
15c
Ishihara K.Kurihara H.Matsumoto M.Yamamoto H. J. Am. Chem. Soc. 1998, 120: 6920 - 16
Corey EJ.Shibata T.Lee TW. J. Am. Chem. Soc. 2002, 124: 3808 - 17
Futatsugi K.Yamamoto H. Angew. Chem. Int. Ed. 2005, 44: 1484 - 18
Liu D.Canales E.Corey EJ. J. Am. Chem. Soc. 2007, 129: 1498 - 19
Marshall JA.Xie S. J. Org. Chem. 1992, 57: 2987 - 20
Lee TW.Corey EJ. J. Am. Chem. Soc. 2001, 123: 1872 - 21
Brown MK.Corey EJ. Org. Lett. 2010, 12: 172 - 22
Mukherjee S.Corey EJ. Org. Lett. 2010, 12: 632 - 23
Shibatomi K.Futatsugi K.Kobayashi F.Iwasa S.Yamamoto H. J. Am. Chem. Soc. 2010, 132: 5625 - 24
Quinkert G.Grosso MD.Doring A.Doring W.Schenkel RI.Bauch M.Dambacher GT.Bats JW.Zimmermann G.Durner G. Helv. Chim. Acta 1995, 78: 1345 - 25
Evans DA.Miller SJ.Lectka T.von Matt P. J. Am. Chem. Soc. 1999, 121: 7559 - 26
Sibi MP.Zhang R.Manyem S. J. Am. Chem. Soc. 2003, 125: 9306 - 27
Ishihara K.Fushimi M. Org. Lett. 2006, 8: 1921 - 28
Rickerby J.Vallet M.Bernardinelli G.Viton F.Kündig EP. Chem. Eur. J. 2007, 13: 3354 - 29
Wang Y.Li H.Wang Y.-Q.Liu Y.Foxman BM.Deng L. J. Am. Chem. Soc. 2007, 129: 6364 - For selected examples of Diels-Alder reactions of fluoroolefins without asymmetric induction, see:
-
30a
Chanteau F.Essers F.Plantier-Royon R.Haufe G.Portella C. Tetrahedron Lett. 2002, 43: 1677 -
30b
Ernet T.Haufe G. J. Chem. Soc., Perkin Trans. 1 2002, 2719 -
30c
Essers M.Mück-Lichtenfeld C.Haufe G. J. Org. Chem. 2002, 67: 4715 -
30d
Ernet T.Maulitz AH.Würthwein E.-U.Haufe G. J. Chem. Soc., Perkin Trans. 1 2001, 1929 -
30e
Sridhar M.Krishna KL.Rao JM. Tetrahedron 2000, 56: 3539 -
30f
Crowley PJ.Percy JM.Stansfield K. Tetrahedron Lett. 1996, 37: 8233 -
30g
Crowley PJ.Percy JM.Stansfield K. Tetrahedron Lett. 1996, 37: 8237 -
30h
Ernet T.Haufe G. Tetrahedron Lett. 1996, 37: 7251 - For diastereoselective Diels-Alder reactions of fluoroolefins with chiral auxiliary, see:
-
31a
Ito H.Saito A.Kakuuchi A.Taguchi T. Tetrahedron 1999, 55: 12741 -
31b
Ito H.Saito A.Taguchi T. Tetrahedron: Asymmetry 1998, 9: 1989 -
31c
Ito H.Saito A.Taguchi T. Tetrahedron: Asymmetry 1998, 9: 1979 - 32
Essers M.Ernet T.Haufe G. J. Fluorine Chem. 2003, 121: 163 - 33
Imura A.Itoh M.Miyadera A. Tetrahedron: Asymmetry 1998, 9: 3047 - 34
Inagaki H.Miyauchi S.Miyauchi RN.Kawato HC.Ohki H.Matsuhashi N.Kawakami K.Takahashi H.Takemura M. J. Med. Chem. 2003, 46: 1005 -
35a
Meyer OGJ.Fröhlich R.Haufe G. Synthesis 2000, 1479 -
35b
Haufe G.Rosen TC.Meyer OGJ.Fröhlich R.Rissanen K. J. Fluorine Chem. 2002, 114: 189 - 36
Hruschka S.Fröhlich R.Kirsch P.Haufe G. Eur. J. Org. Chem. 2007, 141 - 37
Wong A.Welch CJ.Kuethe JT.Vazquez E.Shaimi M.Henderson D.Davies IW.Hughes DL. Org. Biomol. Chem. 2004, 2: 168 - 38
Nakazato A.Kumagai T.Sakagami K.Yoshikawa R.Suzuki Y.Chaki S.Ito H.Taguchi T.Nakanishi S.Okuyama S. J. Med. Chem. 2000, 43: 4893 - 39
Honma M.Sawada T.Fujisawa Y.Utsugi M.Watanabe H.Umino A.Matsumura T.Hagihara T.Takano M.Nakada M. J. Am. Chem. Soc. 2003, 125: 2860 - 40
Martin SF.Spaller MR.Liras S.Hartmann B. J. Am. Chem. Soc. 1994, 116: 4493 - 41
Lin W.Charette AB. Adv. Synth. Catal. 2005, 347: 1547 - 42
Charette AB.Juteau H.Lebel H.Molinaro C. J. Am. Chem. Soc. 1998, 120: 11943 - 43
Huang H.Panek J. Org. Lett. 2004, 6: 4383 -
44a
Cui X.Burgess K. Chem. Rev. 2005, 105: 3272 -
44b
Brown JM. In Comprehensive Asymmetric Catalysis Vol. I:Jacobsen E.Pfaltz A.Yamamoto H. Springer-Verlag; Berlin: 1999. p.121 -
44c
Halterman RL. In Comprehensive Asymmetric Catalysis Vol. I:Jacobsen E.Pfaltz A.Yamamoto H. Springer-Verlag; Berlin: 1999. p.183 - 45
Saburi M.Shao L.Sakurai T.Uchida Y. Tetrahedron Lett. 1992, 33: 7877 - 46
Ohta T.Takaya H.Kitamura M.Nagai K.Noyori R.
J. Org. Chem. 1987, 52: 3174 -
47a
Engman M.Diesen JS.Paptchikhine A.Andersson PG. J. Am. Chem. Soc. 2007, 129: 4536 -
47b
Kaukoranta P.Engman M.Hedberg C.Bergquist J.Andersson PG. Adv. Synth. Catal. 2008, 350: 1168 -
48a
Wang C.-J.Sun X.Zhang X. Angew. Chem. Int. Ed. 2005, 44: 4933 -
48b
Sun X.Zhou L.Li W.Zhang X. J. Org. Chem. 2008, 73: 1143 -
49a
Utaka M.Konishi S.Okubo T.Tsuboi S.Takeda A. Tetrahedron Lett. 1987, 28: 1447 -
49b
Utaka M.Konishi S.Mizuoka A.Ohkubo T.Sakai T.Tsuboi S.Takeda A. J. Org. Chem. 1989, 54: 4989 - 50
Utaka M.Konishi S.Takeda A. Tetrahedron Lett. 1986, 27: 4737 - 51
D’Arrigo P.Lattanzio M.Fantoni GP.Servi S. Tetrahedron: Asymmetry 1998, 9: 4021 - 52
Kitazume T.Ishikawa N. Chem. Lett. 1983, 12: 237 - 53
Luo F.Wang P.Gong Y. Tetrahedron Lett. 2010, 51: 1693 -
54a
Katsuki T. In Comprehensive Asymmetric Catalysis Vol. II:Jacobsen E.Pfaltz A.Yamamoto H. Springer-Verlag; Berlin: 1999. p.621 -
54b
Jacobsen EN.Wu MH. In Comprehensive Asymmetric Catalysis Vol. II:Jacobsen E.Pfaltz A.Yamamoto H. Springer-Verlag; Berlin: 1999. p.649 -
54c
Aggarwal VK. In Comprehensive Asymmetric Catalysis Vol. II:Jacobsen E.Pfaltz A.Yamamoto H. Springer-Verlag; Berlin: 1999. p.679 - 55
Gosmini C.Dubuffet T.Sauvêtre R.Normant J.-F. Tetrahedron: Asymmetry 1991, 2: 223 - 56
Kitano Y.Matsumoto T.Wakasa T.Okamoto S.Shimazaki T.Kobayashi Y.Sato F. Tetrahedron Lett. 1987, 28: 6351 - 57
Wong OA.Shi Y. J. Org. Chem. 2009, 74: 8377 -
58a
Tomioka K.Nagaoka Y. In Comprehensive Asymmetric Catalysis Vol. III:Jacobsen E.Pfaltz A.Yamamoto H. Springer-Verlag; Berlin: 1999. p.1105 -
58b
Yamaguchi M. In Comprehensive Asymmetric Catalysis Vol. III:Jacobsen E.Pfaltz A.Yamamoto H. Springer-Verlag; Berlin: 1999. p.1121 - 59
Wang Y.Liu X.Deng L. J. Am. Chem. Soc. 2006, 128: 3928 - 60
Wang B.Wu F.Wang Y.Liu X.Deng L. J. Am. Chem. Soc. 2007, 129: 768 - 61
Li K.Alexakis A. Angew. Chem. Int. Ed. 2006, 45: 7600 - 62
Tsubogo T.Saito S.Seki K.Yamashita Y.Kobayashi S. J. Am. Chem. Soc. 2008, 130: 13321 - 63
Shirahase M.Kanemasa S.Oderaotoshi Y. Org. Lett. 2004, 6: 675 - 64
Bandini M.Cozzi PG.Melchiorre P.Morganti S.Umani-Ronchi A. Org. Lett. 2001, 3: 1153 -
65a
Modern Aldol Reactions
Mahrwald R. Wiley-VCH; Weinheim: 2004. -
65b
Carreira EM. In Comprehensive Asymmetric Catalysis Vol. III:Jacobsen E.Pfaltz A.Yamamoto H. Springer-Verlag; Berlin: 1999. p.997 -
66a
Iseki K.Kuroki Y.Kobayashi Y. Tetrahedron Lett. 1997, 38: 7209 -
66b
Iseki K.Kuroki Y.Kobayashi Y. Synlett 1998, 437 -
66c
Iseki K.Kuroki Y.Kobayashi Y. Tetrahedron 1999, 55: 2225 -
67a
Kiyooka S.-I.Shahid KA. Tetrahedron: Asymmetry 2000, 11: 1537 -
67b
Kiyooka S.-I.Shahid KA. Tetrahedron Lett. 2000, 41: 2633 - 68
Imashiro R.Kuroda T. J. Org. Chem. 2003, 68: 974 - 69
Gondi VB.Hagihara K.Rawal VH. Angew. Chem. Int. Ed. 2009, 48: 776 -
70a
Enantioselective Organocatalysis
Dalko PI. Wiley-VCH; Weinheim: 2007. -
70b
Berkessel A.Gröger H. Asymmetric Organocatalysis Wiley-VCH; Weinheim: 2005. -
70c
List B. In Modern Aldol Reactions Vol. 1:Mahrwald R. Wiley-VCH; Weinheim: 2004. p.161 - 71
Zhong G.Fan J.Barbas CF. Tetrahedron Lett. 2004, 45: 5681 - For biocatalytic asymmetric direct aldol reaction of fluoroacetone, see:
-
72a
Barbas CF.Heine A.Zhong G.Hoffmann T.Gramatikova S.Björnestedt R.List B.Anderson J.Stura EA.Wilson IA.Lerner R. Science 1997, 278: 2085 -
72b
Hoffmann T.Zhong G.List B.Shabat D.Anderson J.Gramatikova S.Lerner R.Barbas CF. J. Am. Chem. Soc. 1998, 120: 2768 -
73a
Xu X.-Y.Wang Y.-Z.Cun L.-F.Gong L.-Z. Tetrahedron: Asymmetry 2007, 18: 237 -
73b
Chen X.-H.Luo S.-W.Tang Z.Cun L.-F.Mi A.-Q.Jiang Y.-Z.Gong L.-Z. Chem. Eur. J. 2007, 13: 689 - 74
He L.Tang Z.Cun L.-F.Mi A.-Q.Jiang Y.-Z.Gong L.-Z. Tetrahedron 2006, 62: 346 - 75
Sato K.Kuriyama M.Shimazawa R.Morimoto T.Kakiuchi K.Shirai R. Tetrahedron Lett. 2008, 49: 2402 -
76a
Guillena G.Hita MC.Nájera C. Tetrahedron: Asymmetry 2007, 18: 1272 -
76b
Guillena G.Hita MC.Nájera C.Viózquez SF. J. Org. Chem. 2008, 73: 5933 - 77
Xu X.-Y.Wang Y.-Z.Gong L.-Z. Org. Lett. 2007, 9: 4247 - 78
Pan Y.Zhao Y.Ma T.Yang Y.Liu H.Jiang Z.Tan C.-H. Chem. Eur. J. 2010, 16: 779 - 79
Arai S.Oku M.Ishida T.Shioiri T. Tetrahedron Lett. 1999, 40: 6785 - 80
Thierry B.Perrard T.Audouard C.Plaquevent J.-C.Cahard D. Synthesis 2001, 1742 - 81
Ding C.Maruoka K. Synlett 2009, 664 - 82
Mohr JT.Behenna DC.Harned AM.Stoltz BM. Angew. Chem. Int. Ed. 2005, 44: 6924 - 83
Nakamura M.Hajra A.Endo K.Nakamura E. Angew. Chem. Int. Ed. 2005, 44: 7248 - 84
Burger EC.Barron BR.Tunge JA. Synlett 2006, 2824 - 85
Bélanger É.Cantin K.Messe O.Tremblay M.Paquin J.-F. J. Am. Chem. Soc. 2007, 129: 1034 - 86
Bélanger É.Pouliot M.-F.Paquin J.-F. Org. Lett. 2009, 11: 2201 - 87
Bélanger É.Houzé C.Guimond N.Cantin K.Paquin J.-F. Chem. Commun. 2008, 3251 - 88
Jiang Z.Pan Y.Zhao Y.Ma T.Lee R.Yang Y.Huang K.-W.Wong MW.Tan C.-H. Angew. Chem. Int. Ed. 2009, 48: 3627 - 89
Cui H.-F.Yang Y.-Q.Chai Z.Li P.Zheng C.-W.Zhu S.-Z.Zhao G. J. Org. Chem. 2010, 75: 117 - 90
Han X.Luo J.Liu C.Lu Y. Chem. Commun. 2009, 2044 - 91
Li H.Zhang S.Yu C.Song X.Wang W. Chem. Commun. 2009, 2136 - 92
Oh Y.Kim SM.Kim DY. Tetrahedron Lett. 2009, 50: 4674 - 93
Prakash GKS.Wang F.Stewart T.Mathew T.Olah GA. Proc. Natl. Acad. Sci. U.S.A. 2009, 106: 4090 - 94
Shibatomi K.Yamamoto H. Angew. Chem. Int. Ed. 2008, 47: 5796 - 95
Frantz R.Hintermann L.Perseghini M.Broggini D.Togni A. Org. Lett. 2003, 5: 1709 - 96
Jereb M.Togni A. Chem. Eur. J. 2007, 13: 9384 - 97
Huber DP.Stanek K.Togni A. Tetrahedron: Asymmetry 2006, 17: 658 - 98
Mang JY.Kwon DG.Kim DY. J. Fluorine Chem. 2009, 130: 259 -
99a
He R.Wang X.Hashimoto T.Maruoka K. Angew. Chem. Int. Ed. 2008, 47: 9466 -
99b
He R.Maruoka K. Synthesis 2009, 2289 - 100
Nakamura S.Kaneeda M.Ishihara K.Yamamoto H.
J. Am. Chem. Soc. 2000, 122: 8120 - 101
Reynolds NT.Rovis T. J. Am. Chem. Soc. 2005, 127: 16406 - 102
Vora HU.Rovis T. J. Am. Chem. Soc. 2010, 132: 2860
References
Endo/exo nomenclature is related to the stereochemistry of the carbonyl substituent.