4,4′-disubstituted-L-proline catalyzes the direct asymmetric Michael addition of aldehydes to nitrostyrenes

Advanced Synthesis and Catalysis

Volumn 349, Issue 10, 2007, Pages 1629-1632

  Gu, Liu Qun ^a   Zhao, Gang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

4 dimethylaminopyridine (DMAP); Diastereoselectivity; Disubstituted L prolines; Enantioselectivity; Michael addition; Organocatalysis

Indexed keywords

EID: 34547158079     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600640     Document Type: Article

References (46)

1. For recent reviews on asymmetric Michael addition reactions, see: a) K. Tomioka, Y. Nagaoka, M. Yamaguchi, in: Comprehensive Asymmetric Catalysis, Vol. I, chap. 31.1 and 31.2, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, New York, 1999, pp. 1105-1139;
2. b) N. Krause, A. Hoffmann-Röder, Synthesis 2001, 171-196;
3. c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894;
4. d) J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726-1728;
5. e) J. Christoffers, Angew. Chem. Int. Ed. 2003, 42, 1688-1690;
6. f) W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 57, 580-591.
7. S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975-2978.
8. a) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425;
9. b) J. M. Betancort. C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740.
10. D. Enders, A. Seki, Synlett 2002, 26-28.
11. a) A. J. A. Cobb, D. A. Longbottom, D. M. Shaw, S. V. Ley, Chem. Commun. 2004, 1808-1809;
12. b) A. J. A. Cobb, D. M. Shaw, D. A. Longbottom, J. B. Gold, S. V. Ley, Org. Biomol. Chem. 2005, 3, 84-96.
13. a) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737-3740;
14. b) N. Mase, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Org. Lett. 2004, 6, 2527-2530;
15. c) J. M. Betancort, K. Sakthivel, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Synthesis 2004, 1509-1521;.
16. a) A. Alexakis, O. Andrey, Org. Lett. 2002, 4, 3611-3614;
17. b) O. Andrey, A. Alexakis, G. Bernardinelli, Org. Lett. 2003, 5, 2559-2562;
18. c) O. Andrey, A. Alexakis, A. Tomassini, G. Bernardinelli, Adv. Synth. Catal. 2004, 346, 1147-1168.
19. T. Ishii, S. Fujioka, Y. Sekiguchi, H. Kotsuki, J. Am. Chem. Soc. 2004, 126, 9558-9559.
20. For recent chiral urea- and thiourea-catalyzed reactions, see: a) M. S. Taylor, E. N. Jacobsen, Angew. Chem. Int. Ed. 2006, 45, 1520-1543;
21. b) R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. Int. Ed. 2005, 44, 6576-6579;
22. c) S. H. Mccooey, S. J. Connon Angew. Chem. Int. Ed. 2005, 44, 6367-6370;
23. d) A. Berkessel, F. Cleemann, S. Mukherjee, T. N. Muller, J. Lex, Angew. Chem. Int. Ed. 2005, 44, 807-811;
24. e) J. Wang, H. Li, X. Yu, L. Zu, W. Wang, Org. Lett. 2005, 7, 4293-4296;
25. f) T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119-125;
26. g) T. P. Yoon, E. N. Jacobsen, Angew. Chem. Int. Ed. 2005, 44, 466-468.
27. L. Zu, J. Wang, H. Li, W. Wang, Org. Lett. 2006, 8, 3077-3079.
28. Y. Xu, A. Cordova, Chem. Commun. 2006, 460-462.
29. C.-L. Cao, M-C. Ye, X-L. Sun, Y. Tang, Org. Lett. 2006, 8, 2901-2904.
30. S. V. Pansare, K. Pandya, J. Am. Chem. Soc. 2006, 128, 9624-9625.
31. W. Wang, J. Wang, H. Li, Angew. Chem. Int. Ed. 2005, 44, 1369-1371.
32. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. Int. Ed. 2005, 44, 4212-4215.
33. S. Mosse, M. Laars, K. Kriis, T. Ranger, A. Alexakis, Org. Lett. 2006, 8, 2559-2562.
34. C. Palomo, S. Vera, A. Mielgo, E. Gomez-Bengoa, Angew. Chem. Int. Ed. 2006, 45, 5984-5987.
35. a) M. P. Lalonde, Y Chen, E. N. Jacobsen, Angew. Chem. Int. Ed. 2006, 45, 6366-6370;
36. b) E. Reyes, J. L. Vicario, D. Badia, L. Carrillo, Org. Lett. 2006, 8, 6135-6138.
37. L. Q. Gu, M. L. Yu, X. Y. Wu, Y. Z. Zhang, G. Zhao, Adv. Synth. Catal. 2006, 348, 2223-2228.
38. a) Y. Sohtome, A. Tanatani, Y. Hashimoto, Kazuo Nagasawa, Tetrahedron Lett. 2004, 45, 5589-5592;
39. b) S.-H. Chen, B.-C. Hong, C.-F. Su, S. Sarshar, Tetrahedron Lett. 2005, 46, 8899-8903.
40. For details, see the Supporting Information.
41. a) S. J. Blarer, D. Seebach, Chem. Ber. 1983, 116, 3086-3096;
42. b) R. Häner, T. Laube, D. Seebach, Chimia 1984, 38, 255-257;
43. c) D. Seebach, A. K. Beck, J. Golinski, J. N. Hay, T. Laube, Helv. Chim. Acta 1985, 68, 162-172;
44. d) D. Seebach, J. Golinski, Helv. Chim. Acta 1981, 64, 1413-1423.
45. M. L. Clarke, J. A. Fuentes, Angew. Chem. Int. Ed. 2007, 46, 930.
46. When the reactants, catalyst and DMAP were mixed, the solution became cloudy while the solution is very clear if DMAP was not added. In point of fact, we presumed that the salt of the catalyst and DMAP may form. However, we have no further experimental evidence to confirm it.