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Synthesis 2007(7): 959-980
DOI: 10.1055/s-2007-965968
DOI: 10.1055/s-2007-965968
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Sulfa-Michael Additions
Further Information
Received
19 January 2007
Publication Date:
28 February 2007 (online)
Publication History
Publication Date:
28 February 2007 (online)
Abstract
Numerous asymmetric methods have been developed over the past 30 years to effect the Michael reaction of sulfur donors and Michael acceptors. Many of these stoichiometric and catalytic methods are complementary to one another, each having a certain range of substrate tolerance. Organocatalysis has a place at the origin of this field in the discovery of cinchona alkaloid catalyzed sulfa-Michael reactions. At the same time, it is involved in the current state-of-the-art as several elegant tandem processes that employ secondary amine catalysts and involve initial sulfa-Michael additions have been developed.
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1 Introduction
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2 Stoichiometric Reactions
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2.1 Chiral Michael Acceptors
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2.2 Chiral Sulfur Donors
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2.3 Tandem Sulfa-Michael/Meerwein-Ponndorf-Verley Reduction Reactions
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2.4 Formal Sulfa-Michael Additions by Intramolecular Sulfur Transfer
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3 Chiral-Metal-Complex-Catalyzed Reactions
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4 Organocatalyzed Reactions
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4.1 Cinchona Alkaloid Catalysts
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4.2 Tertiary Amino Alcohol Catalysts
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4.3 Secondary Amine Catalysts
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4.4 Urea-Based Catalysts
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5 Polymer-Catalyzed Reactions
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6 Miscellaneous Methods
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7 Conclusions and Outlook
Key words
sulfur compounds - asymmetric Michael additions - alpha,beta-unsaturated carbonyl compounds - tandem reactions - organocatalysis
- 1
Fraústo da Silva JR.Williams RJP. The Biological Chemistry of the Elements Oxford University Press; New York: 2001. - 2
Parry RJ. In Comprehensive Natural Products Chemistry Vol. 1:Barton D.Nakanishi K. Pergamon Press; Oxford: 1999. p.825 - 3
Kondo T.Mitsudo T.-A. Chem. Rev. 2000, 100: 3205 - 4
Sibi M.Manyem S. Tetrahedron 2000, 56: 8033 - 5
Okazaki R. In Organosulfur Chemistry Vol. 1:Page P. Academic Press; London: 1995. p.225 - 6
Perlmutter P. Conjugate Addition Reactions in Organic Synthesis Pergamon Press; Oxford: 1992. - 7
Berner OM.Tedeschi L.Enders D. Eur. J. Org. Chem. 2002, 1877 - 8
Krause N.Hoffmann-Röder A. Synthesis 2001, 171 - 9
Enders D.Saint-Dizier A.Lannou M.-I.Lenzen A. Eur. J. Org. Chem. 2005, 29 - 10
Wynberg H. Top. Stereochem. 1986, 16: 87 - 11
Kamimura A. J. Synth. Org. Chem. Jpn. 2004, 62: 705 - 12
Berkessel A.Gröger H. Asymmetric Organocatalysis Wiley-VCH; Weinheim: 2005. - 13
Effenberger F.Isak H. Chem. Ber. 1989, 122: 553 - 14
Kim BH.Lee HB.Hwang JK.Kim YG. Tetrahedron: Asymmetry 2005, 16: 1215 - 15
Tseng T.-C.Wu M.-J. Tetrahedron: Asymmetry 1995, 6: 1633 - 16
Tomioka K.Muraoka A.Kanai M. J. Org. Chem. 1995, 60: 6188 - 17
Miyata O.Shinada T.Ninomiya I.Naito T. Tetrahedron Lett. 1991, 32: 3519 - 18
Miyata O.Shinada T.Ninomiya I.Naito T. Tetrahedron 1997, 53: 2421 - 19
Inoue H.Takeo S.Kawazu M.Kugita H. Yakugaku Zasshi 1973, 93: 729 - 20
Giordano C.Restelli A.Villa M.Annunziata R. J. Org. Chem. 1991, 56: 2270 - 21
Seyden-Penne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis John Wiley and Sons; New York: 1995. - 22
Tsai W.-J.Lin Y.-T.Uang B.-J. Tetrahedron: Asymmetry 1994, 5: 1195 - 23
Lin C.-H.Yang K.-S.Pan J.-F.Chen K. Tetrahedron Lett. 2000, 41: 6815 - 24
Miyata O.Shinada T.Kawakami N.Taji K.Ninomiya I.Naito T.Date T.Okamura K. Chem. Pharm. Bull. 1992, 40: 2579 - 25
Wu M.-J.Wu C.-C.Tseng T.-C. J. Org. Chem. 1994, 59: 7188 - 26
Cousins G.Falshaw A.Hoberg JO. Org. Biomol. Chem. 2004, 2: 2272 - 27
Nishimura K.Tsubouchi H.Ono M.Hayama T.Nagaoka Y.Tomioka K. Tetrahedron Lett. 2003, 44: 2323 - 28
Fabbri D.Delogu G.De Lucchi O. Tetrahedron: Asymmetry 1993, 4: 1591 - 30
Nishide K.Ohsugi S.-I.Shiraki H.Tamakita H.Node M. Org. Lett. 2001, 3: 3121 - 31
Nishide K.Shigeta Y.Obata K.Node M. J. Am. Chem. Soc. 1996, 118: 13103 - 32
Node M.Nishide K.Shigeta Y.Shiraki H.Obata K. J. Am. Chem. Soc. 2000, 122: 1927 - 33
Shiraki H.Nishide K.Node M. Tetrahedron Lett. 2000, 41: 3437 - 34
Ozeki M.Nishide K.Teraoka F.Node M. Tetrahedron: Asymmetry 2004, 14: 895 - 35
Nishide K.Ozeki M.Kunishige H.Shigeta Y.Patra PK.Hagimoto Y.Node M. Angew. Chem. Int. Ed. 2003, 42: 4515 ; Angew. Chem. 2003, 115, 4653 - 36
Ozeki M.Hashimoto D.Nishide K.Kajimoto T.Node M. Tetrahedron: Asymmetry 2005, 16: 1663 - 37
Palomo C.Oiarbide M.Dias F.Ortiz A.Linden A. J. Am. Chem. Soc. 2001, 123: 5602 - 38
Ortiz A.Quintero L.Hernández H.Maldonado S.Mendoza G.Bernès S. Tetrahedron Lett. 2003, 44: 1129 - 39
Ortiz A.Hernández H.Mendoza G.Quintero L.Bernès S. Tetrahedron Lett. 2005, 46: 2243 - 40
Palomo C.Oiarbide M.López R.González PB.Gómez-Bengoa E.Saá JM.Linden A. J. Am. Chem. Soc. 2006, 128: 15236 - 41
Palomo C.Oiarbide M.Dias F.López R.Linden A. Angew. Chem. Int. Ed. 2004, 43: 3307 ; Angew. Chem. 2004, 116, 3369 - 42
Kinoshita H.Takahashi N.Iwamura T.Watanabe S.-I.Kataoka T.Muraoka O.Tanabe G. Tetrahedron Lett. 2005, 46: 7155 - 43
Kataoka T.Kinoshita H.Kinoshita S.Osamura T.Watanabe S.Iwamura T.Muraoka O.Tanabe G. Angew. Chem. Int. Ed. 2003, 42: 2889 ; Angew. Chem. 2003, 115, 2995 - 44
Kinoshita H.Osamura T.Mizuno K.Kinoshita S.Iwamura T.Watanabe S.Kataoka T.Tanabe G. Chem. Eur. J. 2006, 12: 3896 - 45
Manickam G.Sundararajan G. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1997, 36: 516 - 46
Manickam G.Sundararajan G. Tetrahedron: Asymmetry 1997, 13: 2271 - 47
Manickam G.Sundararajan G. Tetrahedron 1999, 55: 2721 - 48
Trost BM.VanVranken DL.Bingel C. J. Am. Chem. Soc. 1992, 114: 9327 - 49
Nishimura K.Ono M.Nagaoka Y.Tomioka K. J. Am. Chem. Soc. 1997, 119: 12974 - 50
Tomioka K.Okuda M.Nishimura K.Manabe S.Kanai M.Nagaoka Y.Koga K. Tetrahedron Lett. 1998, 39: 2141 - 51
Nishimura K.Tomioka K. J. Org. Chem. 2002, 67: 431 - 52
Nishimura K.Tomioka K. Yakugaku Zasshi 2003, 123: 9 - 53
Nishimura K.Ono M.Nagaoka Y.Tomioka K. Angew. Chem. Int. Ed. 2001, 40: 440 ; Angew. Chem. 2001, 113, 454 - 54
Emori E.Arai T.Sasai H.Shibasaki M. J. Am. Chem. Soc. 1998, 120: 4043 - 55
Emori E.Iida T.Shibasaki M. J. Org. Chem. 1999, 64: 5318 - 56
Sawada D.Kanai M.Shibasaki . J. Am. Chem. Soc. 2000, 122: 10521 - 57
Kanemasa S.Oderaotoshi Y.Yamamoto H.Tanaka J.Wada E.Curran DP. J. Org. Chem. 1997, 62: 6454 - 58
Kanemasa S.Oderaotoshi Y.Yamamoto H.Tanaka J.Wada E. J. Am. Chem. Soc. 1998, 120: 12355 - 59
Kanemasa S.Oderaotoshi Y.Wada E. J. Am. Chem. Soc. 1999, 121: 8675 - 60
Kanemasa S. J. Synth. Org. Chem. Jpn. 2003, 61: 1073 - 61
Kanemasa S.Ito K. Eur. J. Org. Chem. 2004, 4741 - 62
Nakajima M.Saito M.Shiro M.Hashimoto S. J. Am. Chem. Soc. 1998, 120: 6419 - 63
Saito M.Nakajima M.Hashimoto S. Chem. Commun. 2000, 1851 - 64
Saito M.Nakajima M.Hashimoto S. Tetrahedron 2000, 56: 9589 - 65
Kobayashi S.Ogawa C.Kawamura M.Sugiura M. Synlett 2001, 983 - 66
Sauerland SJK.Kiljunen E.Koskinen AMP. Tetrahedron Lett. 2006, 47: 1291 - 67
Matsumoto K.Watanabe A.Uchida T.Ogi K.Katsuki T. Tetrahedron Lett. 2004, 45: 2385 - 68
Pracejus H.Wilke F.-W.Hanemann K. J. Prakt. Chem. 1977, 319: 219 - 69
Wynberg H.Helder R. Tetrahedron Lett. 1975, 16: 4057 - 70
Helder R.Arends R.Bolt W.Hiemstra H.Wynberg H. Tetrahedron Lett. 1977, 18: 2181 - 71
Hiemstra H.Wynberg H. J. Am. Chem. Soc. 1981, 103: 417 - 72
Dijkstra GDH.Kellogg RM.Wynberg H. Recl. Trav. Chim. Pays-Bas 1989, 108: 195 - 73
Colonna S.Re A.Wynberg H. J. Chem. Soc., Perkin Trans. 1 1981, 547 - 74
Ahuja RR.Natu AA.Gogte VN. Tetrahedron Lett. 1980, 21: 4743 - 75
Sera A.Takagi K.Katayama H.Yamada H.Matsumoto K. J. Org. Chem. 1988, 53: 1157 - 76
Kobayashi N.Iwai K. J. Org. Chem. 1981, 46: 1823 - 77
Yamashita H.Mukaiyama T. Chem. Lett. 1985, 14: 363 - 78
Keniya J.Natu AA.Gogte VN. Chem. Ind. (London) 1986, 243 - 79
Kumar A.Salunkhe RV.Rane RA.Dike SY. J. Chem. Soc., Chem. Commun. 1991, 485 - 80
Skarżewski J.Zielińska-Blajet M.Turowska-Tyrk I. Tetrahedron: Asymmetry 2001, 12: 1923 - 81
Zielińska-Blajet M.Kowalczyk R.Skarżewski J. Tetrahedron 2005, 61: 5235 - 82
McDaid P.Chen Y.Deng L. Angew. Chem. Int. Ed. 2002, 41: 338 ; Angew. Chem. 2002, 114, 348 - 83
Mukaiyama T.Ikegawa A.Suzuki K. Chem. Lett. 1981, 10: 165 - 84
Suzuki K.Ikegawa A.Mukaiyama T. Bull. Chem. Soc. Jpn. 1982, 55: 3277 - 85
Suzuki K.Ikegawa A.Mukaiyama T. Chem. Lett. 1982, 11: 899 - 86
Palomo C.Mielgo A. Angew. Chem. Int. Ed. 2006, 45: 7876 ; Angew. Chem. 2006, 118, 8042 - 87
Marigo M.Schulte T.Franzén J.Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 15710 - 88
Enders D.Grondal C.Hüttl MRH. Angew. Chem. Int. Ed. 2007, 46: in press ; Angew. Chem. 2007, 119, in press - 89
Brandau S.Maerten E.Jørgensen KA. J. Am. Chem. Soc. 2006, 128: 14986 - 90
Wang W.Li H.Wang J.Zu L. J. Am. Chem. Soc. 2006, 128: 10354 - 91
Rios R.Sundén H.Ibrahem I.Zhao G.-L.Eriksson L.Córdova A. Tetrahedron Lett. 2006, 47: 8547 - 92
Rios R.Sundén H.Ibrahem I.Zhao G.-L.Córdova A. Tetrahedron Lett. 2006, 47: 8679 - 93
Okino T.Hoashi Y.Takemoto Y. J. Am. Chem. Soc. 2003, 125: 12672 - 94
Okino T.Nakamura S.Furukawa T.Takemoto Y. Org. Lett. 2004, 6: 625 - 95
Okino T.Hoashi Y.Furukawa T.Xu X.Takemoto Y. J. Am. Chem. Soc. 2005, 127: 119 - 96
Li B.-J.Jiang L.Liu M.Chen Y.-C.Ding L.-S.Wu Y. Synlett 2005, 603 - 97
Li H.Wang J.Zu L.-S.Wang W. Tetrahedron Lett. 2006, 47: 2585 - 98
Li H.Zu L.Wang J.Wang W. Tetrahedron Lett. 2006, 47: 3145 - 99
Kobayashi N.Iwai K. J. Am. Chem. Soc. 1978, 100: 7071 - 100
Hodge P.Khoshdel E.Waterhouse J.Fréchet JMJ. J. Chem. Soc., Perkin Trans. 1 1985, 2327 - 101
Athawale V.Manjrekar N. Tetrahedron Lett. 2001, 42: 4541 - 102
Sundararajan G.Prabagaran N. Org. Lett. 2001, 3: 389 - 103
Kobayashi O. inventors; Japanese Patent 2002275267A. - 104
Toda F.Tanaka K.Sato J. Tetrahedron: Asymmetry 1993, 4: 1771 - 105
Sakuraba H.Tanaka Y.Toda F. J. Inclusion Phenom. Macrocyclic Chem. 1991, 11: 195 - 106
Schuurman RJW.Grimbergen RFP.Scheeren HW.Nolte RJM. Recl. Trav. Chim. Pays-Bas 1996, 115: 357 - 107
Kitazume T.Murata K. J. Fluorine Chem. 1988, 39: 75 - 108
Svedendahl M.Hult K.Berglund P. J. Am. Chem. Soc. 2005, 127: 17988
References
Enders, D.; Doszczak, L. RWTH Aachen, 2003, unpublished results.