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Communication | Special issue | Vol 67, No. 2, 2006, pp.495-501
Published online, 18th November, 2005
DOI: 10.3987/COM-05-S(T)41
Catalytic Asymmetric Michael Reaction under Phase-transfer Catalysis: Construction of Chiral Tetrasubstituted Carbon and Its Application to the Synthesis of a Chiral Pyrrolidone

Shigeru Arai,* Fumie Takahashi, Riichiro Tsuji, and Atsushi Nishida*

*Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

A catalytic asymmetric Michael reaction using Schiff bases promoted by D2-symmetrical ammonium salts as phase-transfer catalysts is described. The reaction of glycine Schiff base (1a) gave the Michael adduct with up to 91% ee and tetrasubstituted carbons was also constructed using alanine Schiff base (3a) with up to 63% ee.