Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2559-2561

  Andrey, Olivier ^a   Alexakis, Alexandre ^a   Bernardinelli, Gérald ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; DIAMINE; ENAMINE; HYDROGEN; KETOL; NITRO DERIVATIVE; NITROGEN; PYRROLIDINE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; CHIRALITY; HYDROGEN BOND; MICHAEL ADDITION; STEREOCHEMISTRY;

EID: 0141563562     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0348755     Document Type: Article

References (43)

1. For recent reviews on this subject, see: (a) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (b) List, B. Tetrahedron 2002, 58, 5573. (c) List, B. Synlett 2001, 1675. (d) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
2. For recent reviews on this subject, see: (a) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (b) List, B. Tetrahedron 2002, 58, 5573. (c) List, B. Synlett 2001, 1675. (d) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
3. For recent reviews on this subject, see: (a) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (b) List, B. Tetrahedron 2002, 58, 5573. (c) List, B. Synlett 2001, 1675. (d) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
4. For recent reviews on this subject, see: (a) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481. (b) List, B. Tetrahedron 2002, 58, 5573. (c) List, B. Synlett 2001, 1675. (d) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
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7. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
8. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
9. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
10. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
11. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
12. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
13. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
14. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
15. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
16. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
17. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
18. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
19. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
20. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
21. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
22. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
23. For recent examples of L-proline-catalyzed reactions, see the following. Aldol reaction: (a) Northrup, A. B.; MacMilan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798. (b) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301. (c) Chowdari, N. S.; Ramachary, D. B.; Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2002, 43, 9591. (d) Cordova, A.; Notz, W.; Barbas III, C. F. Chem. Commun. 2002, 3024. (e) Bogevig, A.; Kumaragurubaran, N.; Anker Jorgensen, K. Chem. Commun. 2002, 620. (f) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (g) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. (h) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395. Mannich reaction: (i) Cordova, A.; Barbas III, C. F. Tetrahedron Lett. 2003, 44, 1923. (j) Watanabe, S.; Cordova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519. (k) Cordova, A.; Watanabe, S.-i.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866. (l) Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199. Conjugate addition: (m) Enders, D.; Seki, A. Synlett 2002, 26. (n) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423. α-Amination: (o) List, B. J. Am. Chem. Soc. 2002, 124, 5656. (p) Kumaragurubaran, N.; Juhl, K.; Zhuang, W.; Bogevig, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2002, 124, 6254. (q) Bogevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
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43. 3, R = 0.030, ωR = 0.031 (See Supporting Information for further details).