An enantioselective Baylis-Hillman reaction catalyzed by chiral phosphines under atmospheric pressure

Chemical Communications

Volumn , Issue 12, 1998, Pages 1271-1272

  Hayase, Tadakatsu ^a   Shibata, Takanori ^a   Soai, Kenso ^a   Wakatsuki, Yasuo ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001161458     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a802594k     Document Type: Article

References (13)

1. Reviews, see: D. Basavaiah, P. D. Rao and R. S. Hyma, Tetrahedron, 1996, 52, 8001;
2. S. E. Drewes and G. H. P. Roos, Tetrahedron, ibid., 1988, 44, 4653;
3. H. M. R. Hoffmann and J. Rabe, Angew. Chem., Int. Ed. Engl., 1985, 24, 4653.
4. For example, see: I. E. Marcó, P. R. Giles, Z. Janousek, H. J. Hindley, J.-P. Declercq, B. Tinant, J. F.-Dupont and J. S. Svensen, Recl. Trav. Chim. Pays-Bas, 1995, 114, 239;
5. M. Bailey, I. E. Marcó and W. D. Ollis, Tetrahedron Lett., 1991, 32, 2687;
6. J. M. Brown, Angew. Chem., Int. Ed. Engl., 1987, 26, 190.
7. T. Oishi, H. Oguri and M. Hirama, Tetrahedron: Asymmetry, 1995, 6, 1241.
8. I. E. Marcó, P. R. Giles and H. J. Hindley, Tetrahedron, 1997, 53, 1015.
9. For diastereoselective Baylis-Hillman reactions, see: L. J. Brzezinski, S. Rafel and J. W. Leathy, J. Am. Chem. Soc., 1997, 119, 4317 and ref. 1.
10. For the use of trialkylphosphines in non-asymmetric Baylis-Hillman reaction, see: S. Rafel and J. W. Leathy, J. Org. Chem., 1997, 62, 1521.
11. Bis(diphenylphosphino)butane (CHIRAPHOS) was utilized as a catalyst in the reaction of an N-tosyl imine with methyl acrylate but no asymmetric induction was reported to be observed: S. Bertenshaw and M. Kahn, Tetrahedron Lett., 1989, 30, 2731. Intramolecular enantioselective reaction using chiral phosphine was reported (14% ee):
12. F. Roth, P. Crygak and G. Fráter, Tetrahedron Lett., 1992, 33, 1045.
13. For early examples of the use of BINAP in enantioselective hydrogenation: R. Noyori and H. Takaya, Acc. Chem. Res., 1990, 23, 345.