Non-Linear Effects in Asymmetric Reactions: Negative and Positive Stereoselectivity in the Formation of Homoleptic 1:2 Metal to Ligand Complexes of Chiral 1,9-Disubstituted Semicorrin Ligands

Chimia

Volumn 57, Issue 10, 2003, Pages 581-585

  Guicher, Nathalie ^b   Stoeckli Evans, Helen ^b   Bernauer, Klaus ^a  

^a UNIVERSITÉ DE NEUCHÂTEL   (Switzerland)

^b NONE

Author keywords

Asymmetric reactions; Negative and positive stereoselectivity; Non linear effects

Indexed keywords

CARBONYL DERIVATIVE; CHELATE; COBALT; COBALT COMPLEX; COPPER; COPPER COMPLEX; DICARBOXYLIC ACID DERIVATIVE; DIETHYL 5 CYANOSEMICORRIN 1,9 DICARBOXYLATE; DIMETHYL 5 CYANOSEMICORRIN 1,9 DICARBOXYLATE; ESTER; FUNCTIONAL GROUP; LIGAND; METAL COMPLEX; NICKEL; NICKEL COMPLEX; NITROGEN; OXYGEN; OXYGEN DERIVATIVE; PALLADIUM; PALLADIUM COMPLEX; UNCLASSIFIED DRUG; ZINC COMPLEX;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC CATALYSIS; ATOM; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; MOLECULAR INTERACTION; MOLECULE; NONLINEAR SYSTEM; NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0242720926     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/000942903777678849     Document Type: Article

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11. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
12. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
13. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
14. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
15. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
16. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
17. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
18. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
19. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
20. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
21. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
22. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
23. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
24. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
25. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
26. N. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028; R. Noyori, M. Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49; N. Iwasawa, Y. Hayashi, H. Sakurai, K. Narasaka, Chem. Lett. 1989, 1581; M. Terada, K. Mikami, T. Nakai, J. Chem. Soc., Chem. Commun. 1990, 1623; K. Mikami, M. Terada, S. Narisada, T. Nakai, Synlett 1992, 255; M. Mikami, J. Chem. Soc., Chem. Commun. 1994, 833; K. Mikami, Y Motoyama, M. Terada, Inorg. Chim. Acta 1994, 222, 71; C. Bolm, Tetrahedron: Asymmetry 1991, 2, 701; C. Bolm, G. Schlinloff, K. Harms, Chem. Ber. 1992, 125, 1191; C. Bolm, M. Ewald, M. Felder, Chem. Ber. 1992, 125, 1205; C. Bolm, J. Müller, G. Schlingloff, M. Zehnder, M. Neuburger, J. Chem. Soc., Chem. Commun. 1993, 182; S. Kanemasa, Y. Oderaptoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, D.P. Curran, J. Am. Chem Soc. 1998, 120, 3074; K. Tanaka, J. Matsui, Y. Kawabata, H. Suzuki, A. Wanatabe, J. Chem. Soc., Chem. Commun. 1991, 1632; B.E. Rossiter, G. Miao, N.M. Swingle, N. Eguchi, A.E. Hernandez, R.G. Patterson, Tetrahedron: Asymmetry, 1992, 2, 231; H. Sasai, T. Suzuki, M. Itoh, M. Shibasaki, Tetrahedron Lett. 1993, 34, 851; N. Kotmasu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529; G.E. Heck, D. Krishnamurphy, M.C. Grier, J. Org. Chem. 1993, 58, 6543; D.A. Evans, S.G. Nelson, M.R. Cagné, A.R. Muci, J. Am. Chem. Soc. 1993, 115, 9800; Q.L. Zhou, A. Pfaltz, Tetrahedron 1994, 50, 4467; R.W. Barnhardt, X. Wang, P. Noheda, S.H. Bergens, J. Whelan, B. Bosnich, Tetrahedron 1994, 50, 4335; A.H.M. de Vries, J.F.G.A. Jansen, B.L. Feringa, Tetrahedron 1994, 50, 4479; M. Kitamura, S. Suga, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800; H.B. Kagan, Synlett 2001, 880; H.B. Kagan, Adv. Synth. Cat. 2001, 243, 227; T. Ohga, S. Umeda, Y. Kwanami, Tetrahedron 2001, 57, 4825.
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