Tetrahedron Letters

Efficient Baylis–Hillman reactions promoted by mild cooperative catalysts and their application to catalytic asymmetric synthesis

YMA Yamada, S Ikegami

Index: Yamada, Yoichi M. A.; Ikegami, Shiro Tetrahedron Letters, 2000 , vol. 41, # 13 p. 2165 - 2169

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Citation Number: 175

Abstract

Baylis–Hillman reactions were promoted by mild cooperative catalysts of tributylphosphine with phenols such as (±)-1, 1′-bi-2-naphthol (BINOL) in THF to give α-methylene-β- hydroxyalkanones in high yield. The reactions proceeded much faster in the presence of 1, 1′-bi-2-naphthol than in its absence. The 1H NMR studies suggested that 1, 1′-bi-2- naphthol functions as a Brønsted acid to activate the carbonyl group of an aldehyde and a ...