Chemistry Letters

An efficient synthesis of 3, 4-dihydropyran-2-one derivatives by Lewis base-catalyzed tandem Michael addition and lactonization

T Tozawa, H Fujisawa, T Mukaiyama

Index: Tozawa, Takashi; Fujisawa, Hidehiko; Mukaiyama, Teruaki Chemistry Letters, 2004 , vol. 33, # 11 p. 1454 - 1455

Full Text: HTML

Citation Number: 18

Abstract

A convenient one-pot preparation of 3, 4-dihydropyran-2-one derivatives by Michael addition of silyl enolate derived from phenyl ester with α, β-unsaturated ketones in the presence of a Lewis base catalyst such as tetrabutylammonium phenoxide was developed. In this catalytic cycle, 3, 4-dihydropyran-2-ones were produced in good to excellent yields via intramolecular cyclization of in situ formed Michael-adducts.