An asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: an efficient approach to the enantioselective …

MT Crimmins, AL Choy

Index: Crimmins, Michael T.; Choy, Allison L. Journal of the American Chemical Society, 1999 , vol. 121, # 24 p. 5653 - 5660

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Citation Number: 174

Abstract

A strategy is described for the enantioselective construction of medium-ring cyclic ethers by merging the asymmetric aldol addition of glycolates with a ring-closing metathesis reaction. Cyclic ethers of seven-, eight-, and nine-membered rings are readily available through a ring- closing metathesis without cyclic conformational constraints, by exploiting the acyclic conformational bias of the gauche effect. A short formal synthesis of the eight-membered ...