Asymmetric Morita-Baylis-Hillman reactions of 2-cyclohexen-1-one catalyzed by chiral biaryl-based bis(thiourea) organocatalysts

Tetrahedron Letters

Volumn 52, Issue 47, 2011, Pages 6234-6237

  Nakayama, Yuki ^a   Gotanda, Takashi ^a   Ito, Katsuji ^a  

^a FUKUOKA UNIVERSITY OF EDUCATION   (Japan)

Author keywords

Allylic alcohol; Bis(thiourea); Morita Baylis Hillman reaction; Organocatalyst

Indexed keywords

2 CYCLOHEXENONE; ALDEHYDE; ALLYL ALCOHOL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOUREA;

ARTICLE; ASYMMETRIC SYNTHESIS; BAYLIS HILLMAN REACTION; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 80054856379     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.064     Document Type: Article

References (24)

1. For reviews: D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811
2. G. Masson, C. Housseman, and J. Zhu Angew. Chem., Int. Ed. 46 2007 4614
3. D. Basavaiah, B.S. Reddy, and S.S. Badsara Chem. Rev. 110 2010 5547
4. Y. Iwabuchi, M. Nakatani, N. Yokoyama, and S. Hatakeyama J. Am. Chem. Soc. 121 1999 10219
5. N.T. McDougal, and S.E. Schaus J. Am. Chem. Soc. 125 2003 12094
6. N.T. McDougal, W.L. Trevellini, S.A. Rodgen, L.T. Kliman, and S.E. Schaus Adv. Synth. Catal. 346 2004 1231
7. Y. Sohtome, A. Tanatani, Y. Hashimoto, and K. Nagasawa Tetrahedron Lett. 45 2004 5589
8. Y. Sohtome, N. Takemura, R. Takagi, Y. Hashimoto, and K. Nagasawa Tetrahedron 64 2008 9423
9. J. Wang, H. Li, X. Yu, L. Zu, and W. Wang Org. Lett. 7 2005 4293
10. A. Berkessel, K. Roland, and J.M. Neudörfl Org. Lett. 8 2006 4195
11. A. Lattanzi Synlett 2007 2106
12. M. Shi, and X.-G. Liu Org. Lett. 10 2008 1043
13. A. Bugarin, and B.T. Connell Chem. Commun. 46 2010 2644
14. J.E. Imbriglio, M.M. Vasbinder, and S.J. Miller Org. Lett. 5 2003 3741
15. M.M. Vasbinder, J.E. Imbriglio, and S.J. Miller Tetrahedron 62 2006 11450
16. H. Tang, P. Gao, T. Zhao, Z. Zhou, L. He, and C. Tang Catal. Commun. 8 2007 1811
17. H. Tang, G. Zhao, Z. Zhou, P. Gao, L. He, and C. Tang Eur. J. Org. Chem. 2008 126
18. K. Yuan, L. Zhang, H.-L. Song, Y. Hu, and X.-Y. Wu Tetrahedron Lett. 49 2008 6262
19. J.-J. Gong, K. Yuan, and X.-Y. Wu Tetrahedron: Asymmetry 2117 2009 20
20. K. Oh, J.-Y. Li, and J. Ryu Org. Biomol. Chem. 8 2010 3015
21. J. Shah, Z. Yacob, A. Bunge, and J. Liebscher Synlett 2010 2079
22. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, and R. Noyori J. Am. Chem. Soc. 118 1996 2521
23. M. Mizuno, and T. Shioiri Chem. Commun. 22 1997 2165
24. A.S. Thompson, G.R. Humphrey, A.M. DeMarco, D.J. Mathre, and E.J.J. Grabowski J. Org. Chem. 58 1993 5886