Direct asymmetric organocatalytic Michael reactions of α,α- disubstituted aldehydes with β-nitrostyrenes for the synthesis of quaternary carbon-containing products

Organic Letters

Volumn 6, Issue 15, 2004, Pages 2527-2530

  Mase, Nobuyuki ^a,b   Thayumanavan, Rajeswari ^a   Tanaka, Fujie ^a   Barbas III, Carlos F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b SHIZUOKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 PYRROLIDINYLMETHYL)PYRROLIDINE; ALDEHYDE DERIVATIVE; CARBON; PYRROLIDINE DERIVATIVE; STYRENE DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; MICHAEL ADDITION; SYNTHESIS;

ALDEHYDES; AMINES; CARBON; CATALYSIS; MOLECULAR STRUCTURE; PROLINE; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM; STYRENES;

EID: 4043184288     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049196o     Document Type: Article

References (43)

1. Enamine-based organocatalytic Michael reactions: (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441-4444. (b) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737-3740. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611-3614. (d) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559-2561. (e) Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (g) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Synthesis 2004, 1509-1521.
2. Enamine-based organocatalytic Michael reactions: (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441-4444. (b) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737-3740. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611-3614. (d) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559-2561. (e) Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (g) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Synthesis 2004, 1509-1521.
3. Enamine-based organocatalytic Michael reactions: (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441-4444. (b) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737-3740. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611-3614. (d) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559-2561. (e) Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (g) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Synthesis 2004, 1509-1521.
4. Enamine-based organocatalytic Michael reactions: (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441-4444. (b) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737-3740. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611-3614. (d) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559-2561. (e) Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (g) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Synthesis 2004, 1509-1521.
5. Enamine-based organocatalytic Michael reactions: (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441-4444. (b) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737-3740. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611-3614. (d) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559-2561. (e) Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (g) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Synthesis 2004, 1509-1521.
6. Enamine-based organocatalytic Michael reactions: (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441-4444. (b) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737-3740. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611-3614. (d) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559-2561. (e) Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (g) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Synthesis 2004, 1509-1521.
7. Enamine-based organocatalytic Michael reactions: (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441-4444. (b) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737-3740. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611-3614. (d) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559-2561. (e) Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260. (g) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Synthesis 2004, 1509-1521.
8. Iminium-based organocatalytic Michael reactions: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173. (c) Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894-7895. (e) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192-1194. (f) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955-4957. (g) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (h) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272-1277.
9. Iminium-based organocatalytic Michael reactions: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173. (c) Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894-7895. (e) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192-1194. (f) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955-4957. (g) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (h) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272-1277.
10. Iminium-based organocatalytic Michael reactions: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173. (c) Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894-7895. (e) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192-1194. (f) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955-4957. (g) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (h) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272-1277.
11. Iminium-based organocatalytic Michael reactions: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173. (c) Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894-7895. (e) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192-1194. (f) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955-4957. (g) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (h) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272-1277.
12. Iminium-based organocatalytic Michael reactions: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173. (c) Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894-7895. (e) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192-1194. (f) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955-4957. (g) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (h) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272-1277.
13. Iminium-based organocatalytic Michael reactions: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173. (c) Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894-7895. (e) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192-1194. (f) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955-4957. (g) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (h) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272-1277.
14. Iminium-based organocatalytic Michael reactions: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173. (c) Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894-7895. (e) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192-1194. (f) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955-4957. (g) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (h) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272-1277.
15. Iminium-based organocatalytic Michael reactions: (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172-1173. (c) Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894-7895. (e) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192-1194. (f) Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955-4957. (g) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (h) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272-1277.
16. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
17. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
18. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
19. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
20. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
21. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
22. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
23. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
24. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
25. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
26. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
27. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
28. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
29. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
30. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
31. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
32. Recent direct organocatalyic reactions using aldehyde and ketone donors: (a) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983-1986. (b) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558-560. (c) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem., Int. Ed. 2004, 43, 1112-1115. (d) Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791. (e) Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450-451. (f) Bogevig, A.; Sunden, H.; Cordova, A. Angew. Chem., Int. Ed. 2004, 43, 1109-1112. (g) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108-4109. (h) Notz, W.; Tanaka, F.; Watanabe, S.; Chowdari, N. S.; Turner, J. M.; Thayumanavan, R.; Barbas, C. F., III J. Org. Chem. 2003, 68, 9624-9634. (i) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (j) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448-2449. (k) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Synlett 2003, 1910-1914. (l) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (m) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett 2003, 1906-1909. (n) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843. (o) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867. (p) Watanabe, S.; Cordova, A., Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519-4522. (q) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, in press.
33. Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420-2423.
34. Mase, N.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2003, 5, 4369-4372.
35. Fluorogenic Michael acceptor: (a) Tanaka, F.; Thayumanavan, R.; Barbas, C. F., III. J. Am. Chem. Soc. 2003, 125, 8523-8528. (b) Tanaka, F.; Thayumanavan, R.; Mase, N.; Barbas, C. F., III. Tetrahedron Lett. 2004, 45, 325-328. See also fluorogenic aldol acceptor: (c) Tanaka, F.; Mase, N.; Barbas, C. F., III. J. Am. Chem. Soc. 2004, 126, 3692-3693.
36. Fluorogenic Michael acceptor: (a) Tanaka, F.; Thayumanavan, R.; Barbas, C. F., III. J. Am. Chem. Soc. 2003, 125, 8523-8528. (b) Tanaka, F.; Thayumanavan, R.; Mase, N.; Barbas, C. F., III. Tetrahedron Lett. 2004, 45, 325-328. See also fluorogenic aldol acceptor: (c) Tanaka, F.; Mase, N.; Barbas, C. F., III. J. Am. Chem. Soc. 2004, 126, 3692-3693.
37. Fluorogenic Michael acceptor: (a) Tanaka, F.; Thayumanavan, R.; Barbas, C. F., III. J. Am. Chem. Soc. 2003, 125, 8523-8528. (b) Tanaka, F.; Thayumanavan, R.; Mase, N.; Barbas, C. F., III. Tetrahedron Lett. 2004, 45, 325-328. See also fluorogenic aldol acceptor: (c) Tanaka, F.; Mase, N.; Barbas, C. F., III. J. Am. Chem. Soc. 2004, 126, 3692-3693.
38. For additional studies of amine-acid combination catalysts in organocatalytic reactions, see ref 1f and: Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177.
39. We used DMSO to dissolve the diamine 10/TFA catalyst. Ratio of DMSO/solvent was 30/70.
40. Typical Procedure for Table 2 entry 14 and Table 3. A catalyst stock solution (1.0 M in 2-PrOH) was prepared as a mixture of (S)-(+)-1-(2- pyrrolidinylmethyl)pyrrolidine (0.5 mmol) and trifluoroacetic acid (0.5 mmol) in 2-PrOH (0.5 mL, HPLC grade) before use. β-Nitrostyrene 14 (0.5 mmol) was dissolved in 2-PrOH (0.85 mL), and isobutyraldehyde 13a (1.0 mmol) was added. To the mixture was added the catalyst stock solution (1.0 M in 2-PrOH, 0.15 mL, 0.15 mmol) at 4°C. The reaction mixture was stirred at 4°C for the indicated time and then purified by flash silica gel column chromatography without further workup to provide Michael product 15a.
41. 2) = 0.0740(0.1795).
42. Nie, Z.; Schweitzer, P.; Roberts, A. J.; Madamba, S. G.; Moore, S. D.; Siggins, G. R. Science 2004, 303, 1512-1514.
43. Scarpi, D.; Lo Galbo, F.; Occhiato, E. G.; Guarna, A. Tetrahedron: Asymmetry 2004, 15, 1319-1324.