A Modified Thermodynamically Controlled Deracemization of 2-Allylcyclohexanone and Its Application to Asymmetric Synthesis of (R)-(−)-Epilachnene

doi:10.1246/CL.2004.516

Paper

A Modified Thermodynamically Controlled Deracemization of 2-Allylcyclohexanone and Its Application to Asymmetric Synthesis of (R)-(−)-Epilachnene

Published Mar 30, 2004 · Hiroto Kaku, Natsuko Okamoto, Aya Nakamaru

Chemistry Letters

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8

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Abstract

The efficiency of thermodynamically controlled deracemization was influenced considerably by the solvent used. Based on this finding, an improved method was developed, by which 2-allylcyclohexanone was converted to the R-isomer of 93% ee in 72% yield. As an application of the method, (R)-(-)-epilachnene, an antipode of the defensive droplets from the Mexican bean beetle, Epilachna varivestis, was synthesized in short steps.

Study Snapshot

The improved method for thermodynamically controlled deracemization of 2-allylcyclohexanone enables efficient conversion to the R-isomer of 93% ee in 72% yield, enabling the asymmetric synthesis of (R)-(-)-epilachnene.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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A Modified Thermodynamically Controlled Deracemization of 2-Allylcyclohexanone and Its Application to Asymmetric Synthesis of (R)-(−)-Epilachnene

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