Organocatalytic, enantioselective conjugate addition of nitroalkanes to nitroolefins

Advanced Synthesis and Catalysis

Volumn 348, Issue 15, 2006, Pages 2047-2050

  Wang, Jian ^a   Li, Hao ^a   Zu, Liansuo ^a   Jiang, Wei ^a   Wang, Wei ^a,b  

^a UNIVERSITY OF NEW MEXICO   (United States)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Asymmetric catalysis; C C bond formation; Michael addition; Organic catalysis

Indexed keywords

EID: 33750525814     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600247     Document Type: Article

References (44)

1. P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
2. For recent reviews of asymmetric Michael addition reactions, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840-3864;
3. P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2001, 40, 3726;
4. b) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
5. P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 43, 5138;
6. c) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877;
7. J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726;
8. J. Christoffers, A. Baro, Angew. Chem. Int. Ed. 2003, 42, 1688;
9. e) M. Sibi, S. Manyem, Tetrahedron 2001, 56, 8033.
10. For selected examples of organocatalytic asymmetric Michael addition of stabilized carbanions to α,β-unsaturated systems, see: a) T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672;
11. b) F. Wu, H. Li, R. Hong, L. Deng, Angew. Chem. 2006, 118, 961;
12. F. Wu, H. Li, R. Hong, L. Deng, Angew. Chem. Int. Ed. 2006, 45, 947;
13. c) J. Wang, H. Li, W. Duan, L. Zu, W. Wang, Org. Lett. 2005, 7, 4713;
14. d) Y. Hoashi, T. Okino, Y. Takemoto, Angew. Chem. Int. Ed. 2005, 44, 4032;
15. e) E. J. Corey, F.-Y. Zhang, Org. Lett. 2000, 2, 4257;
16. f) M. Yamaguchi, T. Shiraishi, M. Hirama, J. Org. Chem. 1996, 67, 3520.
17. K. Funabashi, Y. Saida, M. Kanai, T. Arai, H. Sasai, M. Shibasaki, Tetrahedron Lett. 1998, 39, 7557.
18. M. S. Taylor, D. N. Zalatan, A. M. Lerchner, E. N. Jacobsen, J. Am. Chem. Soc. 2005, 127, 1313.
19. A. P. Davis, K. J. Dempsey, Tetrahedron: Asymmetry 1995, 6, 2829.
20. S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975.
21. B. Vakulya, S. Varga, A. Csampai, T. Soós, Org. Lett. 2005, 7, 1967.
22. a) N. Halland, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2002, 67, 8331;
23. b) A. Prieto, N. Halland, K. A. Jørgensen, Org. Lett. 2005, 7, 3897.
24. a) T. Ooi, K. Doda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 9022;
25. b) T. Ooi, S. Fujioka, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 11790.
26. N. Ono, The Nitro Group in Organic Synthesis Wiley-VCH, New York, 2001.
27. [14] and a) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423;
28. b) D. Enders, A. Seki, Synlett 2002, 26;
29. c) N. Mase, R. Thayumanavan, F. Tanaka, C. F. Barbas, III, Org. Lett. 2004, 6, 2527;
30. d) O. Andrey, A. Alexakis, G. Bernardinelli, Org. Lett. 2003, 5, 2559;
31. e) T. Ishii, S. Fiujioka, Y. Sekiguchi, H. Kotsuki, J. Am. Chem. Soc. 2004, 126, 9558;
32. f) A. J. A. Cobb, D. A. Longbottom, D. M. Shaw, S. V. Ley, Chem. Commun. 2004, 1808;
33. g) Y. Hayashi, T. Gotoh, T. Hayasji, M. Shoji, Angew. Chem. 2005, 117, 4284;
34. Y. Hayashi, T. Gotoh, T. Hayasji, M. Shoji, Angew. Chem. Int. Ed. 2005, 44, 4212;
35. h) R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. 2005, 117, 6734;
36. R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. Int. Ed. 2005, 44, 6576;
37. i) Y.-M. Xu, W.-B. Zou, H. Sunden, I. Ibrahem, A. Córdova, Adv. Synth. Catal. 2006, 348, 418;
38. j) J. Wang, H. Li, L.-S. Zu, W. Wang, Org. Lett. 2006, 8, 1391.
39. S.-F. Lu, D.-M. Du, J. Xu, S.-W. Zhang, J. Am. Chem. Soc. 2006, 128, 7418.
40. For selected examples of unasymmetric synthesis of 1,3-dinitro compounds, see: a) M. D. Alcantara, F. C. Escribano, A. Gómez-Sánchez, M. J. Diánez, M. D. Estrada, A. López-Castro, S. Pérez-Garrido, Synthesis 1996, 64;
41. b) R. Ballini, G. Bosica, D. Fiorini, A. Palmieri, Synthesis 2004, 1938.
42. (S)-Pyrrolidine trifluoromethansulfonamide VIII has been used for catalyzing the Michael addition of aldehydes and ketones to nitroolefins: a) W. Wang, J. Wang, H. Li, Angew. Chem. 2005, 117, 1393;
43. W. Wang, J. Wang, H. Li, Angew. Chem. Int. Ed. 2005, 44, 1369;
44. b) J. Wang, H. Li, B.-S. Lou, L.-S. Zu, H. Guo, W. Wang, Chem. Eur. J. 2006, 12, 4321.