Rapid Fluorescent Screening for Bifunctional Amine-Acid Catalysts: Efficient Syntheses of Quaternary Carbon-Containing Aldols under Organocatalysis

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4369-4372

  Mase, Nobuyuki ^a,b   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

ACETIC ACID DERIVATIVE; ACID; AMINE; PYRROLIDINE DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; ENVIRONMENTAL TEMPERATURE; FLUORESCENCE; SCREENING; SYNTHESIS;

ACIDS; AMINES; CARBON; CATALYSIS; SPECTROMETRY, FLUORESCENCE;

EID: 0345359331     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035651p     Document Type: Article

References (37)

1. Review: Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 389-401. Aldol-Tishchenko reaction of naked aldehyde: Mascarenhas, C. M.; Miller, S. P.; White, P. S.; Morken, J. P. Angew. Chem., Int. Ed. 2001, 40, 601-603.
2. Review: Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 389-401. Aldol-Tishchenko reaction of naked aldehyde: Mascarenhas, C. M.; Miller, S. P.; White, P. S.; Morken, J. P. Angew. Chem., Int. Ed. 2001, 40, 601-603.
3. Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169-2178.
4. Selected aldol studies: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (d) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303. (e) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510-2511. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591-9595. (g) Anders, B.; Nagaswamy, K.; Anker, J. K. Chem. Commun. 2002, 620-621. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263. (j) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090-1091.
5. Selected aldol studies: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (d) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303. (e) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510-2511. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591-9595. (g) Anders, B.; Nagaswamy, K.; Anker, J. K. Chem. Commun. 2002, 620-621. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263. (j) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090-1091.
6. Selected aldol studies: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (d) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303. (e) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510-2511. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591-9595. (g) Anders, B.; Nagaswamy, K.; Anker, J. K. Chem. Commun. 2002, 620-621. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263. (j) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090-1091.
7. Selected aldol studies: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (d) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303. (e) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510-2511. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591-9595. (g) Anders, B.; Nagaswamy, K.; Anker, J. K. Chem. Commun. 2002, 620-621. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263. (j) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090-1091.
8. Selected aldol studies: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (d) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303. (e) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510-2511. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591-9595. (g) Anders, B.; Nagaswamy, K.; Anker, J. K. Chem. Commun. 2002, 620-621. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263. (j) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090-1091.
9. Selected aldol studies: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (d) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303. (e) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510-2511. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591-9595. (g) Anders, B.; Nagaswamy, K.; Anker, J. K. Chem. Commun. 2002, 620-621. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263. (j) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090-1091.
10. Selected aldol studies: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (d) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303. (e) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510-2511. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591-9595. (g) Anders, B.; Nagaswamy, K.; Anker, J. K. Chem. Commun. 2002, 620-621. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263. (j) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090-1091.
11. Selected aldol studies: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (d) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303. (e) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510-2511. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591-9595. (g) Anders, B.; Nagaswamy, K.; Anker, J. K. Chem. Commun. 2002, 620-621. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263. (j) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090-1091.
12. Selected aldol studies: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (d) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303. (e) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510-2511. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591-9595. (g) Anders, B.; Nagaswamy, K.; Anker, J. K. Chem. Commun. 2002, 620-621. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263. (j) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090-1091.
13. Selected aldol studies: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395-2396. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267. (c) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177. (d) Cordova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301-303. (e) Kotrusz, P.; Kmentova, I.; Gotov, B.; Toma, S.; Solcaniova, E. Chem. Commun. 2002, 2510-2511. (f) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 9591-9595. (g) Anders, B.; Nagaswamy, K.; Anker, J. K. Chem. Commun. 2002, 620-621. (h) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799. (i) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Qiao, A.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262-5263. (j) Darbre, T.; Machuqueiro, M. Chem. Commun. 2003, 1090-1091.
14. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
15. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
16. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
17. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
18. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
19. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
20. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
21. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
22. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
23. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
24. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
25. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
26. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
27. Recent studies in organocatalysis: (a) Pidathala, C.; Hoang, L.; Vignola, N.; List, B. Angew. Chem., Int. Ed. 2003, 42, 2785-2788. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498-1501. (c) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677-3680. (d) Halland, N.; Aburel, P. S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (e) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17. (f) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479. (g) Melchiorre, P.; Jorgensen, K. A. J. Org. Chem. 2003, 68, 4151-4157. (h) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Org. Lett. 2003, 5, 1685-1688. (i) Bahmanyar, S.; Houk, K. N. Org. Lett. 2003, 5, 1249-1251. (j) Cordova, A.; Barbas, C. F., III. Tetrahedron Lett. 2003, 44, 1923-1926. (k) Liu, H.; Peng, L.; Zhang, T.; Li, Y. New J. Chem. 2003, 27, 1159-1160. (l) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247-4250. (m) Ramachary, D. B.; Chowdari, N. S.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2003, 42, 4233-4237. (n) Hayashi, Y. ; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208-11209.
28. Tanaka, F.; Thayumanavan, R.; Barbas, C. F., III. J. Am. Chem. Soc. 2003, 125, 8523-8528.
29. (a) Kuehne, M. E. J. Am. Chem. Soc. 1959, 81, 5400-5404.
30. (b) Spencer, T. A.; Neel, H. S.; Ward, D. C.; Williamson, K. L. J. Org. Chem. 1966, 31, 434-436.
31. (c) Woodward, R. B. Pure Appl. Chem. 1968, 17, 519-547.
32. (d) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1612-1615.
33. Pyrrolidine-AcOH has been studied in intramolecular aldol reactions; see ref 6b-d. See also: (a) Desmaele, D.; d'Angelo, J. Tetrahedron Lett. 1989, 30, 345-348. (b) Snider, B. B.; Yang, K. J. Org. Chem. 1990, 55, 4392-4399. (c) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 35, 3999-4002. (d) Greco, M. N.; Maryanoff, B. E. Tetrahedron Lett. 1992, 33, 5009-5012.
34. Pyrrolidine-AcOH has been studied in intramolecular aldol reactions; see ref 6b-d. See also: (a) Desmaele, D.; d'Angelo, J. Tetrahedron Lett. 1989, 30, 345-348. (b) Snider, B. B.; Yang, K. J. Org. Chem. 1990, 55, 4392-4399. (c) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 35, 3999-4002. (d) Greco, M. N.; Maryanoff, B. E. Tetrahedron Lett. 1992, 33, 5009-5012.
35. Pyrrolidine-AcOH has been studied in intramolecular aldol reactions; see ref 6b-d. See also: (a) Desmaele, D.; d'Angelo, J. Tetrahedron Lett. 1989, 30, 345-348. (b) Snider, B. B.; Yang, K. J. Org. Chem. 1990, 55, 4392-4399. (c) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 35, 3999-4002. (d) Greco, M. N.; Maryanoff, B. E. Tetrahedron Lett. 1992, 33, 5009-5012.
36. Pyrrolidine-AcOH has been studied in intramolecular aldol reactions; see ref 6b-d. See also: (a) Desmaele, D.; d'Angelo, J. Tetrahedron Lett. 1989, 30, 345-348. (b) Snider, B. B.; Yang, K. J. Org. Chem. 1990, 55, 4392-4399. (c) Barros, M. T.; Santos, A. G.; Godinho, L. S.; Maycock, C. D. Tetrahedron Lett. 1994, 35, 3999-4002. (d) Greco, M. N.; Maryanoff, B. E. Tetrahedron Lett. 1992, 33, 5009-5012.
37. 3 (V = 46.2) and pyrrolidine-p-toluic acid (V = 131.8) gave the aldol product in 82% (15 h) and 91% (5 h) yield, respectively.