The Journal of Organic Chemistry

The Synthesis of Bicyclic Ketols from Cyclohexanones

JA Marshall, WI Fanta

Index: Marshall,J.A.; Fanta,W.I. Journal of Organic Chemistry, 1964 , vol. 29, p. 2501 - 2505

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Citation Number: 78

Abstract

Reaction conditions are defined for the preparation of ketols by Robinson annelation of cyclohexanones. The cis-keto1 I1 and the trans-keto1 I11 are formed stereoselectively from 2-methylcyclohexanone and cyclohexanone using an equimolar quantity of methyl vinyl ketone. The ketol I1 is a convenient source of lO-methyl-l (9)-octalone-2 (I), The scope and stereochemistry of the Michael-aldol reaction sequence is discussed.