Journal of the American Chemical Society

Stereospecific umpolung. alpha.'substitution of ketones via reactions of organocuprates with enol ethers of. alpha.,. beta.-epoxycyclohexanones

JP Marino, JC Jaen

Index: Marino,J.P.; Jaen,J.C. Journal of the American Chemical Society, 1982 , vol. 104, p. 3165

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Citation Number: 68

Abstract

Abstract: The silyl enol ethers of substituted 2, 3-epoxycyclohexanones react with alkyl-and phenylcyanocuprate reagents in a regio-and stereospecific manner to yield, in most cases, the 1.4-trans adducts. Vinylic cuprates show a regioselectivity that is dependent on the substitution pattern of each particular substrate. The stereochemistry of the adducts obtained in these reactions was determined, as well as their conformational preferences, by 'H and ...

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