Stereoselective, Dual-Mode Ruthenium-Catalyzed Ring Expansion of Alkynylcyclopropanols

BM Trost, J Xie, N Maulide

Index: Trost, Barry M.; Xie, Jia; Maulide, Nuno Journal of the American Chemical Society, 2008 , vol. 130, # 51 p. 17258 - 17259

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Citation Number: 55

Abstract

A novel, dual-pathway ring expansion of alkynylcyclopropanols is described. On treatment with a ruthenium catalyst, these compounds undergo highly selective enlargement to either (Z)-alkylidene cyclobutanones or β-substituted cyclopentenones. The unique ability to access the least selective double bond isomers of alkylidene cyclobutanones and the dramatic shift of reactivity observed further illustrate the particular intricacies of ruthenium ...