Journal of the American Chemical Society

Studies in Stereochemistry. XX. Steric Control of Asymmetric Induction in the Preparation of the 3-Cyclohexyl-2-butanol System1

DJ Cram, FD Greene

Index: Cram; Greene Journal of the American Chemical Society, 1953 , vol. 75, p. 6005,6009

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Citation Number: 50

Abstract

The applicability of the “Rule of Steric Control of Asymmetric Induction” to reactions producing diastereomeric mixtures of 3-cyclohexyl-2-butanol has been studied. The reactions of methylmagnesium iodide, methyllithium in ether and methyllithium in pentane with 2-cyclohexylpropana1, and of lithium aluminum hydride and sodium borohydride with 3- cyclohexyl-2-butanone were found to give product balances qualitatively predicted by the ...