Towards perfect catalytic asymmetric synthesis: Dual activation of the electrophile and the nucleophile

Angewandte Chemie - International Edition

Volumn 43, Issue 35, 2004, Pages 4566-4583

  Ma, Jun An ^a,b,c,g   Cahard, Dominique ^a,c,d,e,f  

^a UNIVERSITÉ DE ROUEN   (France)

^b NANKAI UNIVERSITY   (China)

^c University of Rouen ^*  (China)

^d UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^e CARDIFF UNIVERSITY   (United Kingdom)

^f RIKEN   (Japan)

^g HENAN UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Bimetallic complexes; Enantioselectivity; Lewis acids; Nucleophilic addition

Indexed keywords

ASYMETRIC CATALYTIC REACTIONS; DUAL ACTIVATION; LEWIS ACID; LEWIS BASE;

CATALYSIS; CHEMICAL ACTIVATION; CHEMICAL REACTIONS; ENZYMES; MECHANISMS; ORGANIC ACIDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CATALYSTS;

BORANE DERIVATIVE; CARBONYL DERIVATIVE; CYANIDE; EPOXIDE; LEWIS ACID;

ADDITION REACTION; ALDOL REACTION; ALKYLATION; ASYMMETRIC CATALYSIS; MANNICH REACTION; PHOSPHORYLATION; REVIEW; RING OPENING; SILYLATION; STRECKER SYNTHESIS;

EID: 5344224096     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200300635     Document Type: Review

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199. For several examples of catalytic asymmetric epoxidations of olefins, see: a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330; b) S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 8090-8091; c) T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725-2732; d) T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474-9475; for examples of catalytic asymmetric hydrophosphonylation and hydrophosphanation, see: e) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089-3103; f) I. Schlemminger, Y. Saida, H. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825; for examples of catalytic asymmetric ring-opening of epoxides, see: g) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784; h) T. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383-2386; Angew. Chem. Int. Ed. 1998, 37, 2223-2226; i) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
200. For several examples of catalytic asymmetric epoxidations of olefins, see: a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330; b) S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 8090-8091; c) T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725-2732; d) T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474-9475; for examples of catalytic asymmetric hydrophosphonylation and hydrophosphanation, see: e) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089-3103; f) I. Schlemminger, Y. Saida, H. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825; for examples of catalytic asymmetric ring-opening of epoxides, see: g) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784; h) T. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383-2386; Angew. Chem. Int. Ed. 1998, 37, 2223-2226; i) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
201. For several examples of catalytic asymmetric epoxidations of olefins, see: a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330; b) S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 8090-8091; c) T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725-2732; d) T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474-9475; for examples of catalytic asymmetric hydrophosphonylation and hydrophosphanation, see: e) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089-3103; f) I. Schlemminger, Y. Saida, H. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825; for examples of catalytic asymmetric ring-opening of epoxides, see: g) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784; h) T. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383-2386; Angew. Chem. Int. Ed. 1998, 37, 2223-2226; i) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
202. For several examples of catalytic asymmetric epoxidations of olefins, see: a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330; b) S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 8090-8091; c) T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725-2732; d) T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474-9475; for examples of catalytic asymmetric hydrophosphonylation and hydrophosphanation, see: e) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089-3103; f) I. Schlemminger, Y. Saida, H. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825; for examples of catalytic asymmetric ring-opening of epoxides, see: g) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784; h) T. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383-2386; Angew. Chem. Int. Ed. 1998, 37, 2223-2226; i) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
203. For several examples of catalytic asymmetric epoxidations of olefins, see: a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330; b) S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 8090-8091; c) T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725-2732; d) T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474-9475; for examples of catalytic asymmetric hydrophosphonylation and hydrophosphanation, see: e) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089-3103; f) I. Schlemminger, Y. Saida, H. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825; for examples of catalytic asymmetric ring-opening of epoxides, see: g) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784; h) T. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383-2386; Angew. Chem. Int. Ed. 1998, 37, 2223-2226; i) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
204. For several examples of catalytic asymmetric epoxidations of olefins, see: a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330; b) S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 8090-8091; c) T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725-2732; d) T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474-9475; for examples of catalytic asymmetric hydrophosphonylation and hydrophosphanation, see: e) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089-3103; f) I. Schlemminger, Y. Saida, H. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825; for examples of catalytic asymmetric ring-opening of epoxides, see: g) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784; h) T. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383-2386; Angew. Chem. Int. Ed. 1998, 37, 2223-2226; i) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
205. For several examples of catalytic asymmetric epoxidations of olefins, see: a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330; b) S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 8090-8091; c) T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725-2732; d) T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474-9475; for examples of catalytic asymmetric hydrophosphonylation and hydrophosphanation, see: e) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089-3103; f) I. Schlemminger, Y. Saida, H. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825; for examples of catalytic asymmetric ring-opening of epoxides, see: g) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784; h) T. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383-2386; Angew. Chem. Int. Ed. 1998, 37, 2223-2226; i) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
206. For several examples of catalytic asymmetric epoxidations of olefins, see: a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330; b) S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 8090-8091; c) T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725-2732; d) T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474-9475; for examples of catalytic asymmetric hydrophosphonylation and hydrophosphanation, see: e) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089-3103; f) I. Schlemminger, Y. Saida, H. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825; for examples of catalytic asymmetric ring-opening of epoxides, see: g) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784; h) T. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383-2386; Angew. Chem. Int. Ed. 1998, 37, 2223-2226; i) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
207. For several examples of catalytic asymmetric epoxidations of olefins, see: a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329-2330; b) S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 8090-8091; c) T. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725-2732; d) T. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474-9475; for examples of catalytic asymmetric hydrophosphonylation and hydrophosphanation, see: e) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089-3103; f) I. Schlemminger, Y. Saida, H. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818-4825; for examples of catalytic asymmetric ring-opening of epoxides, see: g) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783-4784; h) T. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383-2386; Angew. Chem. Int. Ed. 1998, 37, 2223-2226; i) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252-2260.
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