The Journal of Organic Chemistry

Chemistry of substituted [. alpha.-(carboethoxy) vinyl] cuprates and their synthetic application to cyclopentenone annulations

JP Marino, RJ Linderman

Index: Marino, Joseph Paul; Linderman, Russell J. Journal of Organic Chemistry, 1981 , vol. 46, # 18 p. 3696 - 3702

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Citation Number: 83

Abstract

The conjugate addition of mixed alkyl cuprates to ethyl propiolate generates substituted [a- (carboethoxy)-vinyljcuprates that readily react with acid chlorides of a, p-unsaturated acids to produce a, a '-dienones. These unsaturated ketones bearing an a-carboethoxy group can serve as precursors to annulated cyclopentenones via a Nazarov-type cyclization. With this two-step sequence, it is possible to efficiently prepare substituted cyclopentenones fused ...