Highly enantioselective water-compatible organocatalyst for Michael reaction of ketones to nitroolefins

Organic Letters

Volumn 9, Issue 6, 2007, Pages 1117-1119

  Vishnumaya, ^a   Singh, Vinod K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947605163     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070082x     Document Type: Article

References (37)

1. (a) For a special issue on asymmetric organocatalysis, see: Acc. Chem. Res. 2004, 37, 487.
2. (b) Review: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
3. (c) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
4. (d) Berkessel, A.; Groger, H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005.
5. For reviews on organic reactions in aqueous media, see: (a) Brogan, A. P.; Dickerson, T. J.; Janda, K. D. Angew. Chem., Int. Ed. 2006, 45, 8100.
6. (b) Hayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 8103.
7. (c) Li, C.-J. Chem. Rev. 2005, 105, 3095.
8. (d) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.
9. (e) Li, C.-J.; Chan, T.-H. Organic Reaction in Aqueous Media; Wiley-VCH: Weinheim, Germany, 1997.
10. Raj, M.; Vishnumaya; Ginotra, S. K.; Singh, V. K. Org. Lett. 2006, 8, 4097.
11. (a) Xu, Y.; Cordova, A. Chem. Commun. 2006, 460.
12. (b) Mase, N.; Watanabe, K.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 4966.
13. (c) Zu, L.; Wang, J.; Li, H.; Wang, W. Org. Lett. 2006, 8, 3077.
14. (d) Pansare, S. V.; Pandya, K. J. Am. Chem. Soc. 2006, 128, 9624.
15. (e) Zhu, M.-K.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. Tetrahedron: Asymmetry 2006, 17, 491.
16. (f) Luo, S.; Mi, X.; Zhang, L.; Liu, S.; Xu, H.; Cheng, J.-P. Angew. Chem., Int. Ed. 2006, 45, 3093.
17. (g) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2005, 44, 105.
18. (h) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
19. (i) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369.
20. (j) Tsogoeva, S. B.; Yalalov, D. A.; Hateley, M. J.; Weckbecker, C.; Huthmacher, K. Eur. J. Org. Chem. 2005, 4995.
21. (k) Hayashi, Y.; Gotoh, T.; Hayasji, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212.
22. (l) Vakulya, B.; Varga, S.; Csampai, A.; Soos, T. Org. Lett. 2005, 7, 1967.
23. (m) McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367.
24. (n) Wang, J.; Li, H.; Duan, W.-H.; Zu, L.-S.; Wang, W. Org. Lett. 2005, 7, 4713.
25. (o) Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
26. (p) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558.
27. (q) Cobb, A. J. A.; Longbottom, D. A.; Shaw, D. M.; Ley, S. V. Chem. Commun. 2004, 1808.
28. (r) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527.
29. (s) Kotrusz, P.; Toma, S.; Schmalz, H.-G.; Adler, A. Eur. J. Org. Chem. 2004, 1577.
30. (t) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559.
31. (u) Tian, S.; Ran, H.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900.
32. (v) Enders, D.; Seki, A. Synlett 2002, 26.
33. (w) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
34. For a catalyst that works both in isopropanol and water, see ref 4c.
35. Hawkins, J. M.; Fu, G. C. J. Org. Chem. 1986, 51, 2820.
36. Kleiner, C. M.; Schreiner, P. R. Chem. Commun. 2006, 4315.
37. Seebach, D.; Golinski, J. Helv. Chim. Acta 1981, 64, 1413.