Enantioselective organocatalytic Michael addition reactions between N-heterocycles and nitroolefins

Organic Letters

Volumn 8, Issue 7, 2006, Pages 1391-1394

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

^a UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CINCHONA ALKALOID; NITRO DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

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

EID: 33645952383     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0601794     Document Type: Article

References (43)

1. (a) Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2nd ed.; Pergamon: Oxford, UK, 2002.
2. (b) Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell Science: Oxford, UK, 2000.
3. (c) Eicher, T.; Hauptmann, S. The Chemistry of Heterocylces. 2nd ed.; Wiley-VCH: New York, 2003.
4. Purwanto, M. G. M.; Weisz, K. Curr. Org. Chem. 2003, 7, 427.
5. (a) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959.
6. (b) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442.
7. (c) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2003. 125. 11204.
8. (d) Vanderwal, C. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 14724.
9. Gandelman, M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 2393.
10. (a) Miller, S. J. Acc. Chem. Res. 2004, 37, 601.
11. (b) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134.
12. (c) Hortsmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem., Int. Ed. 2000, 39, 3635.
13. (d) Guerin, D. J.; Horstmann, T. E.; Miller, S. J. Org. Lett. 1999, 1, 1107.
14. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
15. For recent reviews of asymmetric Michael addition reactions, see: (a) Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
16. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
17. (c) Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688.
18. (d) Sibi, M.; Manyem, S. Tetrahedron 2001, 56, 8033.
19. (e) Pinko, P. M. Angew. Chem., Int. Ed. 2004, 43, 2062.
20. (f) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
21. (g) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289.
22. For selected examples of proline and its derivatives promoted organocatalytic asymmetric Michael addition of nitroolefins, see: (a) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 43, 1369.
23. (b) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
24. (c) Enders, D.; Seki, A. Synlett 2002, 26.
25. (d) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III Org. Lett. 2004, 6, 2527.
26. (e) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III Synthesis 2004, 1509.
27. (f) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559.
28. (g) Ishii, T.; Fiujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558.
29. (h) Cobb, A. J. A.; Longbottom, D. A.; Shaw, D. M.; Ley, S. V. Chem. Commun. 2004, 1808.
30. (i) Hayashi, Y.; Gotoh, T.; Hayasji, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212.
31. For Takemoto's amine thiourea catalysts, see: (a) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119 and cited references therein.
32. (b) Berkessel, A.; Cleemann, F.; Mukherjee, S.; Müller, T. N.; Lex, J. Angew. Chem., Int. Ed. 2005, 44, 807.
33. (c) Berkessel, A.; Mukherjee, S.; Cleemann, F.; Müller, T. N.; Lex, J. Chem. Commun. 2005, 1898.
34. For Jacobsen's urea and thiourea catalysts, see: Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558 and cited references therein.
35. For cinchona alkaloids-based derivative catalysts: see: (a) Tian, S.-K.; Chen, Y.-G.; Hang, J.-F.; Tang, L.; McDaid, P.; Deng, L. Acc. Chem. Res. 2004, 37, 621.
36. (b) Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
37. (c) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2005, 44, 105.
38. (d) Tian, S.; Ran, H.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900.
39. (e) Vakulya, B.; Varga, S.; Csampai, A.; Soos, T. Org. Lett. 2005, 7, 1967.
40. Recently, we have developed binaphthyl-based amine thioureas for asymmetric organocatalytic reactions, see: (a) Wang, J.; Li, H.; Duan, W.; Zu, L.; Wang, W. Org. Lett. 2005, 7, 4293.
41. (b) Wang, J.; Li, H.; Yu, X.; Zu, L.; Wang, W. Org. Lett. 2005, 7, 4713.
42. Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; Wiley-VCH: New York, 2005.
43. 2H in pharmacologically active compounds due to their favorable physicochemical properties.