Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones

Chemical Communications

Volumn 47, Issue 13, 2011, Pages 3992-3994

  Wu, Bin ^a   Liu, Guo Gui ^a   Li, Mei Qiu ^a   Zhang, Yong ^a   Zhang, Shao Yun ^a   Qiu, Jun Ru ^a   Xu, Xiao Ping ^a   Ji, Shun Jun ^a   Wang, Xing Wang ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; NITROMETHANE; THIOUREA;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; ENANTIOMER; MICHAEL ADDITION; ONE POT SYNTHESIS; STEREOCHEMISTRY;

EID: 79952663511     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c0cc05418f     Document Type: Article

References (39)

1. T. L. Ho, Carbocycle Construction in Terpene Synthesis, Wiley-VCH, Weinheim, Germany, 1988
2. T. Bui, C. F. Barbas III, Tetrahedron Lett., 2000, 41, 6951
3. S. Yao, M. Johannsen, H. Audrain, R. G. Hazell, K. A. Jøgensen, J. Am. Chem. Soc., 1998, 120, 8599
4. J. Long, J. Hu, X. Shen, B. Ji, K. Ding, J. Am. Chem. Soc., 2002, 124, 10
5. Y. Yuan, J. Long, J. Sun, K. Ding, Chem.–Eur. J., 2002, 8, 5033
6. K. Ding, H. Du, Y. Yuan, J. Long, Chem.–Eur. J., 2004, 10, 2872
7. F. Aznar, A. B. Garcìa, M. A. Cabal, Adv. Synth. Catal., 2006, 348, 2443
8. D. B. Ramachary, N. S. Chowdari, C. F. Barbas III, Angew. Chem., Int. Ed., 2003, 42, 4233
9. Y. Wang, H. Li, Y.-Q. Wang, Y. Liu, B. M. Foxman, L. Deng, J. Am. Chem. Soc., 2007, 129, 6364
10. C. Palomo, A. Mielgo, Angew. Chem., Int. Ed., 2006, 45, 7876
11. B. List, Chem. Commun., 2006, 819
12. J. W. Yang, M. H. Fonseca, B. List, J. Am. Chem. Soc., 2005, 127, 15036
13. Y. Huang, A. M. Walji, C. H. Larsen, D. W. C. MacMillan, J. Am. Chem. Soc., 2005, 127, 15051
14. D. Enders, M. R. M. Hüttl, C. Grondal, G. Raabe, Nature, 2006, 441, 861
15. W. Wang, H. Li, J. Wang, L. Zu, J. Am. Chem. Soc., 2006, 128, 10354
16. C. Schneider, O. Reese, Angew. Chem., Int. Ed., 2000, 39, 2948
17. E. Maudru, G. Singh, R. H. Wightman, Chem. Commun., 1998, 1505
18. R. J. Ferrier, S. Middleton, Chem. Rev., 1993, 93, 2779
19. E. A. Carrie, S. J. Miller, J. Am. Chem. Soc., 2007, 129, 256
20. J. Zhou, B. List, J. Am. Chem. Soc., 2007, 129, 7498
21. N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem., Int. Ed., 2004, 43, 1272
22. J. Pulkkinen, P. S. Aburel, N. Halland, K. A. Jørgensen, Adv. Synth. Catal., 2004, 346, 1077
23. Y. Hoashi, T. Yabuta, Y. Takemoto, Tetrahedron Lett., 2004, 45, 9185
24. L. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem., Int. Ed., 2009, 48, 7196
25. D. B. Ramachary, Y. V. Reddy, B. V. Prakash, Org. Biomol. Chem., 2008, 6, 719
26. E. P. Kohler, R. W. Helmkamp, J. Am. Chem. Soc., 1924, 46, 1267
27. J. Li, W. Xu, G. Chen, T. Li, Ultrason. Sonochem., 2005, 12, 473
28. A. C. Silvanus, B. J. Groombridge, B. I. Andrews, G. Kociok-Köhn, D. R. Carbery, J. Org. Chem., 2010, 75, 7491
29. D. Zhang, X. Xu, J. Tan, Q. Liu, Synlett, 2010, 917
30. M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc., 1998, 120, 4901
31. P. R. Schreiner, A. Wittkopp, Org. Lett., 2002, 4, 217
32. O. Tomotaka, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc., 2003, 125, 12672
33. Y. Sohtome, Y. Hashimoto, K. Nagasawa, Adv. Synth. Catal., 2005, 347, 1643
34. J. Wang, H. Li, X. Yu, L. Zu, W. Wang, Org. Lett., 2005, 7, 4293
35. C.-L. Cao, M.-C. Ye, X.-L. Sun, Y. Tang, Org. Lett., 2006, 8, 2901
36. B. Vakulya, S. Varga, A. Csámpai, T. Soós, Org. Lett., 2005, 7, 1967
37. S. H. McCooey, S. J. Connon, Angew. Chem., Int. Ed., 2005, 44, 6367
38. J. Ye, D. J. Dixon, P. S. Hynes, Chem. Commun., 2005, 4481
39. B. Li, L. Jiang, M. Liu, Y. Chen, L. Ding, Y. Wu, Synlett, 2005, 603