Catalytic enantioselective addition of propionate units to imines: An efficient synthesis of anti-α-methyl-β-amino acid derivatives

Chemistry - A European Journal

Volumn 8, Issue 18, 2002, Pages 4185-4190

  Kobayashi, Shu ^a   Kobayashi, Jun ^a   Ishiani, Haruro ^a   Ueno, Masaharu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

amino acids; Asymmetric catalysis; BINOL derivatives; Mannich reactions; Zirconium

Indexed keywords

AMINO ACIDS; COMPLEXATION; DERIVATIVES; ZIRCONIUM COMPOUNDS;

CHIRAL LIGANDS;

SYNTHESIS (CHEMICAL);

AMINO ACID; AMINO ACID DERIVATIVE; IMINE; PROPIONIC ACID DERIVATIVE;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CHIRALITY; COMPLEX FORMATION; DERIVATIZATION; ENANTIOMER; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CATALYSIS; IMINES; MOLECULAR STRUCTURE; PROPIONATES; STEREOISOMERISM;

EID: 0037120156     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20020916)8:18<4185::AID-CHEM4185>3.0.CO;2-6     Document Type: Article

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14. Examples of asymmetric synthesis of α-alkyl-β-amino carbonyl compounds based on diastereoselective enolate-imine condensations: a) D. J. Hart, C.-S. Lee, W. H. Pirkle, M. H. Hyon. A. Tsipouras. J. Am. Chem. Soc. 1986, 108, 6054; b) C. Gennari, I. Venturini, G. Gislon. G. Schimperna, Tetrahedron Lett. 1987, 28, 227; c) T. Yamada. H. Suzuki, T. Mukaiyama. Chem. Lett. 1987, 293; d) D. A. Evans. F. Urpí, T. C. Sommers. J. S. Clark, M. T. Bilodeau, J. Am. Chem. Soc. 1990, 112. 8215; e) E. J. Corey, C. P. Decicco, R. C. Newbold, Tetrahedron Lett. 1991 32, 5287; f) K. Hattori, M. Miyata. H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 1151; g) D. Enders, D. Ward, J. Adam, G. Raabe, Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981; h) H. Fujieda, M, Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060.
15. Examples of asymmetric synthesis of α-alkyl-β-amino carbonyl compounds based on diastereoselective enolate-imine condensations: a) D. J. Hart, C.-S. Lee, W. H. Pirkle, M. H. Hyon. A. Tsipouras. J. Am. Chem. Soc. 1986, 108, 6054; b) C. Gennari, I. Venturini, G. Gislon. G. Schimperna, Tetrahedron Lett. 1987, 28, 227; c) T. Yamada. H. Suzuki, T. Mukaiyama. Chem. Lett. 1987, 293; d) D. A. Evans. F. Urpí, T. C. Sommers. J. S. Clark, M. T. Bilodeau, J. Am. Chem. Soc. 1990, 112. 8215; e) E. J. Corey, C. P. Decicco, R. C. Newbold, Tetrahedron Lett. 1991 32, 5287; f) K. Hattori, M. Miyata. H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 1151; g) D. Enders, D. Ward, J. Adam, G. Raabe, Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981; h) H. Fujieda, M, Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060.
16. Examples of asymmetric synthesis of α-alkyl-β-amino carbonyl compounds based on diastereoselective enolate-imine condensations: a) D. J. Hart, C.-S. Lee, W. H. Pirkle, M. H. Hyon. A. Tsipouras. J. Am. Chem. Soc. 1986, 108, 6054; b) C. Gennari, I. Venturini, G. Gislon. G. Schimperna, Tetrahedron Lett. 1987, 28, 227; c) T. Yamada. H. Suzuki, T. Mukaiyama. Chem. Lett. 1987, 293; d) D. A. Evans. F. Urpí, T. C. Sommers. J. S. Clark, M. T. Bilodeau, J. Am. Chem. Soc. 1990, 112. 8215; e) E. J. Corey, C. P. Decicco, R. C. Newbold, Tetrahedron Lett. 1991 32, 5287; f) K. Hattori, M. Miyata. H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 1151; g) D. Enders, D. Ward, J. Adam, G. Raabe, Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981; h) H. Fujieda, M, Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060.
17. Examples of asymmetric synthesis of α-alkyl-β-amino carbonyl compounds based on diastereoselective enolate-imine condensations: a) D. J. Hart, C.-S. Lee, W. H. Pirkle, M. H. Hyon. A. Tsipouras. J. Am. Chem. Soc. 1986, 108, 6054; b) C. Gennari, I. Venturini, G. Gislon. G. Schimperna, Tetrahedron Lett. 1987, 28, 227; c) T. Yamada. H. Suzuki, T. Mukaiyama. Chem. Lett. 1987, 293; d) D. A. Evans. F. Urpí, T. C. Sommers. J. S. Clark, M. T. Bilodeau, J. Am. Chem. Soc. 1990, 112. 8215; e) E. J. Corey, C. P. Decicco, R. C. Newbold, Tetrahedron Lett. 1991 32, 5287; f) K. Hattori, M. Miyata. H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 1151; g) D. Enders, D. Ward, J. Adam, G. Raabe, Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981; h) H. Fujieda, M, Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060.
18. Examples of asymmetric synthesis of α-alkyl-β-amino carbonyl compounds based on diastereoselective enolate-imine condensations: a) D. J. Hart, C.-S. Lee, W. H. Pirkle, M. H. Hyon. A. Tsipouras. J. Am. Chem. Soc. 1986, 108, 6054; b) C. Gennari, I. Venturini, G. Gislon. G. Schimperna, Tetrahedron Lett. 1987, 28, 227; c) T. Yamada. H. Suzuki, T. Mukaiyama. Chem. Lett. 1987, 293; d) D. A. Evans. F. Urpí, T. C. Sommers. J. S. Clark, M. T. Bilodeau, J. Am. Chem. Soc. 1990, 112. 8215; e) E. J. Corey, C. P. Decicco, R. C. Newbold, Tetrahedron Lett. 1991 32, 5287; f) K. Hattori, M. Miyata. H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 1151; g) D. Enders, D. Ward, J. Adam, G. Raabe, Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981; h) H. Fujieda, M, Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060.
19. Examples of asymmetric synthesis of α-alkyl-β-amino carbonyl compounds based on diastereoselective enolate-imine condensations: a) D. J. Hart, C.-S. Lee, W. H. Pirkle, M. H. Hyon. A. Tsipouras. J. Am. Chem. Soc. 1986, 108, 6054; b) C. Gennari, I. Venturini, G. Gislon. G. Schimperna, Tetrahedron Lett. 1987, 28, 227; c) T. Yamada. H. Suzuki, T. Mukaiyama. Chem. Lett. 1987, 293; d) D. A. Evans. F. Urpí, T. C. Sommers. J. S. Clark, M. T. Bilodeau, J. Am. Chem. Soc. 1990, 112. 8215; e) E. J. Corey, C. P. Decicco, R. C. Newbold, Tetrahedron Lett. 1991 32, 5287; f) K. Hattori, M. Miyata. H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 1151; g) D. Enders, D. Ward, J. Adam, G. Raabe, Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981; h) H. Fujieda, M, Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060.
20. Examples of asymmetric synthesis of α-alkyl-β-amino carbonyl compounds based on diastereoselective enolate-imine condensations: a) D. J. Hart, C.-S. Lee, W. H. Pirkle, M. H. Hyon. A. Tsipouras. J. Am. Chem. Soc. 1986, 108, 6054; b) C. Gennari, I. Venturini, G. Gislon. G. Schimperna, Tetrahedron Lett. 1987, 28, 227; c) T. Yamada. H. Suzuki, T. Mukaiyama. Chem. Lett. 1987, 293; d) D. A. Evans. F. Urpí, T. C. Sommers. J. S. Clark, M. T. Bilodeau, J. Am. Chem. Soc. 1990, 112. 8215; e) E. J. Corey, C. P. Decicco, R. C. Newbold, Tetrahedron Lett. 1991 32, 5287; f) K. Hattori, M. Miyata. H. Yamamoto, J. Am. Chem. Soc. 1993, 115, 1151; g) D. Enders, D. Ward, J. Adam, G. Raabe, Angew. Chem. 1996, 108, 1059; Angew. Chem. Int. Ed. Engl. 1996, 35, 981; h) H. Fujieda, M, Kanai, T. Kambara, A. Iida, K. Tomioka, J. Am. Chem. Soc. 1997, 119, 2060.
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22. Catalytic asymmetric direct Mannich reactions were recently reported: a) S. Yamasaki, T. Iida, M. Shibasaki, Tetrahedron 1999, 55, 885; b) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083; Angew. Chem. Int. Ed. Engl. 2001, 40, 2995; c) B. List, P. Pojarliev, W. T. Biller. H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827.
23. Catalytic asymmetric direct Mannich reactions were recently reported: a) S. Yamasaki, T. Iida, M. Shibasaki, Tetrahedron 1999, 55, 885; b) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083; Angew. Chem. Int. Ed. Engl. 2001, 40, 2995; c) B. List, P. Pojarliev, W. T. Biller. H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827.
24. Catalytic asymmetric direct Mannich reactions were recently reported: a) S. Yamasaki, T. Iida, M. Shibasaki, Tetrahedron 1999, 55, 885; b) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083; Angew. Chem. Int. Ed. Engl. 2001, 40, 2995; c) B. List, P. Pojarliev, W. T. Biller. H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827.
25. Catalytic asymmetric direct Mannich reactions were recently reported: a) S. Yamasaki, T. Iida, M. Shibasaki, Tetrahedron 1999, 55, 885; b) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083; Angew. Chem. Int. Ed. Engl. 2001, 40, 2995; c) B. List, P. Pojarliev, W. T. Biller. H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827.
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