Chiral phosphinothiourea-catalyzed asymmetric Morita-Baylis-Hillman reactions of acrylates with aromatic aldehydes

Tetrahedron

Volumn 65, Issue 39, 2009, Pages 8185-8190

  Yuan, Kui ^a   Song, Hong Liang ^a   Hu, Yinjun ^a   Wu, Xin Yan ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Acrylate; Asymmetric organocatalysis; Chiral phosphinothiourea; Enantioselective Morita Baylis Hillman reaction

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; PHOSPHINE DERIVATIVE; THIOUREA DERIVATIVE;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 69049101105     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.07.066     Document Type: Article

References (37)

1. Basavaiah D., Rao P.D., and Hyma R.S. Tetrahedron 52 (1996) 8001-8062
2. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811-891
3. Coelho F., and Rossi R.C. Tetrahedron Lett. 43 (2002) 2797-2800
4. Silveira G.P.C., and Coelho F. Tetrahedron Lett. 46 (2005) 6477-6481
5. Trost B.M., Thiel O.R., and Tsui H.-C. J. Am. Chem. Soc. 124 (2002) 11616-11617
6. Iwabuchi Y., Sugihara T., Esumi T., and Hatakeyama S. Tetrahedron Lett. 42 (2001) 7867-7871
7. Iwabuchi Y., Furukawa M., Esumi T., and Hatakeyama S. Chem. Commun. (2001) 2030-2031
8. Trost B.M., Tsui H.-C., and Toste F.D. J. Am. Chem. Soc. 122 (2000) 3534-3535
9. For reviews, see:
10. Langer P. Angew. Chem., Int. Ed. 39 (2000) 3049-3052
11. Basavaiah D., Rao K.V., and Reddy R.J. Chem. Soc. Rev. 36 (2007) 1581-1588
12. Masson G., Housseman C., and Zhu J. Angew. Chem., Int. Ed. 46 (2007) 4614-4628
13. Selected papers on asymmetric MBH and aza-MBH reaction:
14. Shi M., and Xu Y.M. Angew. Chem., Int. Ed. 41 (2002) 4507-4510
15. McDougal N.T., and Schaus S.E. J. Am. Chem. Soc. 125 (2003) 12094-12095
16. Raheem I.T., and Jacobsen E.N. Adv. Synth. Catal. 347 (2005) 1701-1708
17. Wang J., Li H., Yu X.H., Zu L., and Wang W. Org. Lett. 7 (2005) 4293-4296
18. Tang H., Zhao G., Zhou Z., Zhou Q., and Tang C. Tetrahedron Lett. 47 (2006) 5717-5721
19. Shi M., and Liu X.-G. Org. Lett. 10 (2008) 1043-1046
20. Iwabuchi Y., Nakatani M., Yodoyama N., and Hatakeyama S. J. Am. Chem. Soc. 121 (1999) 10219-10220
21. Shi M., and Jiang J.-K. Tetrahedron: Asymmetry 13 (2002) 1941-1947
22. Yang K.-S., Lee W.-D., Pan J.-F., and Chen K. J. Org. Chem. 68 (2003) 915-919
23. Tang H.Y., Zhao G.F., Zhou Z.H., Gao P., He L.N., and Tang C.C. Eur. J. Org. Chem. (2008) 126-135
24. Xu J.Y., Guan Y.Y., Yang S.H., Ng Y.R., Peh G.R., and Tan C.-H. Chem. Asian J. 1 (2006) 724-729
25. Krishna P.R., Kannan V., and Reddy P.V.N. Adv. Synth. Catal. 346 (2004) 603-606
26. Bhuniya D., Narayanan S., Lamba T.S., and Reddy K.V.S.R.K. Synth. Commun. 33 (2003) 3717-3726
27. Hayashi N., Yanagihara K., and Tsuboi S. Tetrahedron: Asymmetry 9 (1998) 3825-3830
28. Adam W., Hoch U., Saha-Moller C.R., and Schreier P. Angew. Chem., Int. Ed. Engl. 32 (1993) 1737-1739
29. Burgess K., and Jennings L.D. J. Org. Chem. 55 (1990) 1138-1139
30. Yuan K., Zhang L., Song H.-L., Hu Y.J., and Wu X.Y. Tetrahedron Lett. 49 (2008) 6262-6264
31. Maja B., Siegfried E.D., Georgia L., and Gregory H.P.R. Synth. Commun. 17 (1987) 795-802
32. Fang Y.-Q., and Jacobsen E.N. J. Am. Chem. Soc. 130 (2008) 5660-5661
33. Cai J.X., Zhou Z.H., Zhao G.F., and Tang C.C. Org. Lett. 4 (2002) 4723-4725
34. He Z., Tang X., Chen Y., and He Z. Adv. Synth. Catal. 348 (2006) 413-417
35. Patra A., Roy A.K., Joshi B.S., Roy R., Batra S., and Bhaduri A.P. Tetrahedron 59 (2003) 663-670
36. Mi X., Luo S., Xu H., Zhang L., and Cheng J.-P. Tetrahedron 62 (2006) 2537-2544
37. Johnson C.L., Donkor R.E., Nawaz E., and Karodia N. Tetrahedron Lett. 45 (2004) 7359-7361