Organic letters

Functionalized Cyclobutenes via Multicomponent Thermal [2+ 2] Cycloaddition Reactions

HM Sheldrake, TW Wallace, CP Wilson

Index: Sheldrake, Helen M.; Wallace, Timothy W.; Wilson, Craig P. Organic Letters, 2005 , vol. 7, # 19 p. 4233 - 4236

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Citation Number: 19

Abstract

Enamine [2+ 2] cycloadditions can be achieved in useful yields simply by stirring a mixture of an aldehyde, diethylamine, a dialkyl fumarate, and potassium carbonate in acetonitrile at 25° C, conditions that are compatible with the presence of a potential leaving group on the β- position of the intermediate enamine. Methylation and elimination of the product cyclobutanes completes a mild nonphotochemical route to functionalized cyclobutenes.