The scope of the direct proline-catalyzed asymmetric addition of ketones to imines

Advanced Synthesis and Catalysis

Volumn 346, Issue 9-10, 2004, Pages 1131-1140

  Notz, Wolfgang ^a   Watanabe, Shin Ichi ^a   Chowdari, Naidu S ^a   Zhong, Guofu ^a   Betancort, Juan M ^a   Tanaka, Fujie ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

oxo amino acids; Asymmetric catalysis; C C bond formation; Imines; Ionic liquids; Mannich type reactions; Organic catalysis

Indexed keywords

AMINO ACID; CYCLOHEXYLGLYCINE; GLYCINE DERIVATIVE; IMINE; KETONE; PROLINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ENANTIOMER; ENANTIOSELECTIVITY; MANNICH REACTION; STEREOCHEMISTRY;

EID: 5144229459     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404114     Document Type: Article

References (67)

1. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
2. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
3. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
4. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
5. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
6. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
7. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
8. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
9. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
10. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
11. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
12. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
13. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
14. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
15. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
16. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
17. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
18. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
19. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
20. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
21. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
22. Aldol reactions: a) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc. 2001, 123, 5260-5267; b) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396; c) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387; d) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303; e) T. Bui, C. F. Barbas III, Tetrahedron Lett. 2000, 41, 6951-6954; f) A. Córdova, W. Notz, C. F. Barbas III Chem. Commun. 2002, 24, 3024-3025; Mannich-type reactions: g) W. Notz, K. Sakthivel, T. Bui, G., Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199 -202; h) W. Notz, Tanaka, F. S. Watanabe, N. S. Chowdari, J. M. Turner, R. Thayumanavan, C. F. Barbas III, J. Org. Chem. 2003, 68, 9624-9634; i) A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842-1843; j) A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866-1867; Michael reactions: k) J. M. Betancort, K. Sakthivel, R. Thayumanavan, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 4441-4444; l) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740; Diels-Alder reactions: m) R. Thayumanavan, B. Dhevalapally, K. Sakthivel, F. Tanaka, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 3817-3820; n) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 6743-6746; one-pot multi-component asymmetric assembly reactions: o) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 9591-9595; p) A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923-1926; q) S. Watanabe, A. Cordova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519-4522; r) N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Org. Lett. 2003, 5, 1685-1688; s) D. B. Ramachary, N. S. Chowdari, C. F Barbas III, Angew. Chem. Int. Ed. 2003, 42, 4233-4237; t) D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Synlett 2003, 1910-1914; u) N. Mase, F. Tanaka, C. F. Barbas III, Org. Lett. 2003, 5, 4369-4372; v) N. Mase, F. Tanaka, C. F. Barbas III, Angew. Chem. Int. Ed. 2004, 43, 2420-2423.
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43. [2q]) did not afford any products in these studies.
44. [2q]
45. [2n,q]
46. [2n,q]
47. [2n,q]
48. As monitored by TLC, the reaction of these donors gave rise to a mixture of multiple products presumably due to self-aldolization or polymerization. This could not be avoided by reducing the donor amount to 2 equivalents, by switching to different solvents, by decreasing the reaction temperature, nor by reducing the catalyst loading to as low as 2%.
49. There have been only single reports of a structurally different α-allylated β-amino ketone and of an α-allylated β-amino acid, respectively; see: a) G. A. Molander, P. J. Stengel, Tetrahedron 1997, 53, 8887-8912; b) J. Wang, Y. Hou, P. Wu, Z. Qu, A. S. C. Chan, Tetrahedron: Asymmetry 1999, 10, 4553-4561.
50. There have been only single reports of a structurally different α-allylated β-amino ketone and of an α-allylated β-amino acid, respectively; see: a) G. A. Molander, P. J. Stengel, Tetrahedron 1997, 53, 8887-8912; b) J. Wang, Y. Hou, P. Wu, Z. Qu, A. S. C. Chan, Tetrahedron: Asymmetry 1999, 10, 4553-4561.
51. E. Hagiwara, A. Fujii, M. Sodeoka, J. Am. Chem. Soc. 1998, 120, 2474-2475.
52. [1a,c]
53. Monitoring the ee of 22a as a function of time revealed that over a period of 72 h no change of ee was detected.
54. N. S. Chowdari, D. B. Ramachary, C. F. Barbas III, Synlett 2003, 1906-1909.
55. a) Enantioselective synthesis, see: A. J. Minnaard, W. H. J. Boesten, H. J. M. Zeegers, Synth. Commun. 1999, 29, 4327-4332 and references therein;
56. b) racemic synthesis, see: H. Pan, X. Yu, D. Wu, Hecheng Huaxue 2001, 9, 263-264.
57. For selected references, see: a) V. M. Garsky, P. K. Lumma, D.-M. Feng, J. Wai, H. G. Ramjit, M. K. Sardana, A. Oliff, R. E. Jones, D. DeFeo-Jones, R. M. Freidinger, J. Med. Chem. 2001, 44, 4216-4224; b) J. S. Tullis, M. J. Laufersweiler, J. C. VanRens, M. G. Natchus, R. G. Bookland, N. G. Almstead, S. Pikul, B. De, L. C. Hsieh, M. J. Janusz, T. M. Branch, S. X. Peng, Y. Y. Jin, T. Hudlicky, K. Oppong, Bioorg. Med. Chem. Lett. 2001, 11, 1975-1979; S. Venkatraman, K. X. Chen, A. Arasappan, F. G. Njoroge, V. M. Girijavallabhan, T.-Y. Chan, B. A. McKittrick, A. J. Prongay, V. S. Madison, Int. Patent WO 0181325, 2001; d) G. Breipohl, W. Holla, H. Jendralla, G. Beck, Int. Patent WO 0155175, 2001.
58. For selected references, see: a) V. M. Garsky, P. K. Lumma, D.-M. Feng, J. Wai, H. G. Ramjit, M. K. Sardana, A. Oliff, R. E. Jones, D. DeFeo-Jones, R. M. Freidinger, J. Med. Chem. 2001, 44, 4216-4224; b) J. S. Tullis, M. J. Laufersweiler, J. C. VanRens, M. G. Natchus, R. G. Bookland, N. G. Almstead, S. Pikul, B. De, L. C. Hsieh, M. J. Janusz, T. M. Branch, S. X. Peng, Y. Y. Jin, T. Hudlicky, K. Oppong, Bioorg. Med. Chem. Lett. 2001, 11, 1975-1979; S. Venkatraman, K. X. Chen, A. Arasappan, F. G. Njoroge, V. M. Girijavallabhan, T.-Y. Chan, B. A. McKittrick, A. J. Prongay, V. S. Madison, Int. Patent WO 0181325, 2001; d) G. Breipohl, W. Holla, H. Jendralla, G. Beck, Int. Patent WO 0155175, 2001.
59. For selected references, see: a) V. M. Garsky, P. K. Lumma, D.-M. Feng, J. Wai, H. G. Ramjit, M. K. Sardana, A. Oliff, R. E. Jones, D. DeFeo-Jones, R. M. Freidinger, J. Med. Chem. 2001, 44, 4216-4224; b) J. S. Tullis, M. J. Laufersweiler, J. C. VanRens, M. G. Natchus, R. G. Bookland, N. G. Almstead, S. Pikul, B. De, L. C. Hsieh, M. J. Janusz, T. M. Branch, S. X. Peng, Y. Y. Jin, T. Hudlicky, K. Oppong, Bioorg. Med. Chem. Lett. 2001, 11, 1975-1979; S. Venkatraman, K. X. Chen, A. Arasappan, F. G. Njoroge, V. M. Girijavallabhan, T.-Y. Chan, B. A. McKittrick, A. J. Prongay, V. S. Madison, Int. Patent WO 0181325, 2001; d) G. Breipohl, W. Holla, H. Jendralla, G. Beck, Int. Patent WO 0155175, 2001.
60. For selected references, see: a) V. M. Garsky, P. K. Lumma, D.-M. Feng, J. Wai, H. G. Ramjit, M. K. Sardana, A. Oliff, R. E. Jones, D. DeFeo-Jones, R. M. Freidinger, J. Med. Chem. 2001, 44, 4216-4224; b) J. S. Tullis, M. J. Laufersweiler, J. C. VanRens, M. G. Natchus, R. G. Bookland, N. G. Almstead, S. Pikul, B. De, L. C. Hsieh, M. J. Janusz, T. M. Branch, S. X. Peng, Y. Y. Jin, T. Hudlicky, K. Oppong, Bioorg. Med. Chem. Lett. 2001, 11, 1975-1979; S. Venkatraman, K. X. Chen, A. Arasappan, F. G. Njoroge, V. M. Girijavallabhan, T.-Y. Chan, B. A. McKittrick, A. J. Prongay, V. S. Madison, Int. Patent WO 0181325, 2001; d) G. Breipohl, W. Holla, H. Jendralla, G. Beck, Int. Patent WO 0155175, 2001.
61. J. R. Porter, J. F. Traverse, A. H. Hoveyda, M. L. Snapper, J. Am. Chem. Soc. 2001, 123, 10409-10410.
62. Recently, another approach toward α-amino lactones such as 32 has been described; see: D. L. J. Clive, J. Zhang, R. Subedi, V. Bouétard, S. Hiebert, R. Ewanuk, J. Org. Chem. 2001, 66, 1233-1241.
63. For example, see: V. W. Cornish, K. M. Hahn, P. G. Schultz, J. Am. Chem. Soc. 1996, 118, 8150-8151.
64. Carbohydrate-based oximes derived from γ-keto amino acids such as 37 were recently used for the synthesis of glycopeptides with clustered oxime-linked glycans; see: L. A. Marcaurelle, Y. Shin, S. Goon, C. R. Bertozzi, Org. Lett. 2001, 3, 3691-3694 and references cited therein.
65. See: R. J. Mears, H. E. Sailes, J. P. Watts, A. Whiting, J. Chem. Soc. Perkin Trans. 1 2000, 3250-3263.
66. Analogous attempts to prepare the corresponding hydrazones in pure form using 2,4-dinitrophenylhydrazine, phenylhydrazine, or methylhydrazine failed. In these cases, either the Schiff bases from the excess ketone donor used were obtained or the corresponding hydrazones were contaminated with by-products that could not be removed.
67. For a recent review of proline organocatalysis, see: W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580-591.