Chiral phosphine Lewis bases in catalytic, asymmetric aza-Morita-Baylis- Hillman reaction

Pure and Applied Chemistry

Volumn 77, Issue 12, 2005, Pages 2105-2110

  Shi, Min ^a   Chen, Lian Hui ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aza Baylis Hillman; Baylis Hillman reaction; Chiral phosphine Lewis bases; Methyl vinyl ketone; N sulfonated imines

Indexed keywords

EID: 29244440395     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200577122105     Document Type: Conference Paper

References (24)

1. (a) E. Ciganek. Org. React. 51, 201 (1997);
2. (b) D. Basavaiah, P. D. Rao, R. S. Hyma. Tetrahedron 52, 8001 (1996).
3. (a) A. B. Baylis and M. E. D. Hillman. Ger. Offen. 2, 155, 113 (1972); Chem. Abstr. 77, 34174q (1972);
4. M. E. D. Hillman and A. B. Baylis. U.S. Patent 3, 743, 669 (1973);
5. (b) K. Morita, Z. Suzuki, H. Hirose. Bull. Chem. Soc. Jpn. 41, 2815 (1968).
6. (a) A. G. M. Barrett, A. S. Cook, A. Kamimura. Chem. Commun. 2533 (1998);
7. (b) N. T. McDougal and S. E. Schaus. J. Am. Chem. Soc. 125, 12094 (2003);
8. (c) Y. Iwabuchi, M. Nakatani, N. Yokoyama, S. Hatakeyama. J. Am. Chem. Soc. 121, 10219 (1999).
9. (a) M. Shi and Y.-M. Xu. Chem. Commun. 1876 (2001);
10. (b) M. Shi and Y.-M. Xu. Angew. Chem., Int. Ed. Engl. 41, 4503 (2002).
11. B. E. Love, P. S. Raje, T. C. Williams. Synlett 493 (1994).
12. (a) Y. Uozumi, A. Tanahashi, S.-Y. Lee. Lee, T. Hayashi. J. Org. Chem. 58, 1945 (1993);
13. (b) J. Kang, S. H. Yu, J. I. Kim, H. G. Cho. Bull. Korean Chem. Soc. 16, 439 (1995);
14. (c) S. Gladiali, S. Medici, G. Pirri, S. Pulacchini, D. Fabbri. Can. J. Chem. 79, 670 (2001);
15. (d) D. Zhao and K.-L. Ding. Org. Lett. 5, 1349 (2003);
16. (e) S.-L. You, X.-L. Hou, L.-X. Dai, B.-X. Cao, J. Sun. Chem. Commun. 1933 (2000);
17. (f) W.-P. Deng, X.-L. Hou, L.-X. Dai, X.-W. Dong. Chem. Commun. 1483 (2000).
18. Bifunctional chiral ligands: see: Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki. Angew. Chem., Int. Ed. Engl. 36, 1871 (1997).
19. (a) J.-W. Han and T. Hayashi. Tetrahedron: Asymmetry 13, 325 (2002);
20. (b) Y. Tian, Q.-C. Yang, T. C. W. Mak, K.-S. Chan. Tetrahedron 58, 3951 (2002).
21. W.-P. Chen, L.-J. Xu, J.-L. Xiao. Tetrahedron Lett. 42, 4275 (2002).
22. I. T. Horvath and J. Rabai. Science 266, 72 (1994);
23. (b) I. T. Horvath. Acc. Chem. Res. 31, 641 (1998);
24. D. P. Curran. Angew. Chem., Int. Ed. Engl. 37, 1175 (1998).