Tetrahedron Letters

Highly efficient synthesis of functionalized tertiary alcohols catalyzed by potassium alkoxide–crown ether complexes

M Hatano, S Suzuki, E Takagi, K Ishihara

Index: Hatano, Manabu; Suzuki, Shinji; Takagi, Eri; Ishihara, Kazuaki Tetrahedron Letters, 2009 , vol. 50, # 26 p. 3171 - 3174

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Citation Number: 17

Abstract

A highly efficient Mukaiyama aldol reaction between ketones and trimethylsilyl enolates in the presence of potassium alkoxide–crown ether complexes as Lewis base catalysts (0.3– 5mol%), which minimized the competing retro-aldol reaction, was developed. These catalysts promoted other addition reactions of trimethylsilyl reagents to ketones and aldimines, such as silyltrifluoromethylation, silylcyanation, and silylphosphonylation. A ...