Asymmetric direct vinylogous michael reaction of activated alkenes to nitroolefins catalyzed by modified cinchona alkaloids

Organic Letters

Volumn 7, Issue 23, 2005, Pages 5293-5296

  Xue, Dong ^a,b   Chen, Ying Chun ^c   Wang, Qi Wei ^a   Cun, Ling Feng ^a   Zhu, Jin ^a   Deng, Jin Gen ^a,b  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c SICHUAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CINCHONA ALKALOID; NITRO DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKENES; CATALYSIS; CINCHONA ALKALOIDS; MOLECULAR STRUCTURE; NITRO COMPOUNDS; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 28244494186     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052283b     Document Type: Article

References (25)

1. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 4th ed.; Kluwer: New York, 2000; p 57.
2. Fuson, R. C. Chem. Rev. 1935, 16, 1.
3. (a) Denmark, S. E.; Heemstra, J. R., Jr.; Beutner, G. L. Angew. Chem., Int. Ed. 2005, 44, 4682.
4. (b) Casiraghi, G.; Zanardi, F. Chem. Rev. 2000, 100, 1929.
5. Bur, S. K.; Martin, S. F. Tetrahedron 2001, 57, 3221.
6. (a) Chen, Y.-C.; Xue, D.; Deng, J.-G.; Cui, X.; Zhu, J.; Jiang, Y.-Z. Tetrahedron Lett. 2004, 45, 1555.
7. (b) Xue, D.; Chen, Y.-C.; Cui, X.; Wang, Q.-W.; Zhu, J.; Deng, J.-G. J. Org. Chem. 2005, 70, 3584.
8. Mansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
9. (a) For selective monoalkylation of vinyl malononitrile, see: Grossman, R. B.; Varner, M. A. J. Org. Chem. 1997, 62, 5235.
10. (b) For the self-dimerization of vinyl malononitriles, see: Weir, M. R. S.; Hyne, J. B. Can. J. Chem. 1964, 42, 1440 and references therein.
11. For recent examples of vinylogous Michael reactions, see: (a) Christoffers, J. Synlett 2001, 723 and references therein.
12. (b) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2004, 6, 3397.
13. During the preparation of this paper, a similar strategy was applied by Jørgensen et al. in γ-amination reactions, see: Poulsen, T. B.; Alemparte, C.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 11614.
14. For recent reviews on organocatalysis, see: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
15. (b) Special issue, Houk, K. N., List, B., Eds.; Acc. Chem. Res. 2004, 37 (8).
16. For reviews on modified cinchona alkaloids, see: (a) Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621.
17. (b) Kacprzak, K.; Gawroński, J. Synthesis 2001, 961.
18. For recent examples, see: (a) Li, H.; Song, J.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2005, 127, 8948.
19. (b) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2005, 44, 105.
20. (c) Poulsen, T. B.; Alemparte, C.; Saaby, S.; Bella, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 2896.
21. (d) Saaby, S.; Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 8120.
22. (e) Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 5672.
23. (f) Papageorgiou, C. D.; de Dios, M. A. C.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 43, 4641.
24. (g) Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
25. Zhang, B.; Zhu, X.-Q.; Lu, J.-Y.; He, J.; Wang, P. G.; Cheng, J.-P. J. Org. Chem. 2003, 68, 3295.