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Communication | Regular issue | Vol 55, No. 1, 2001, pp.9-12
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9058
■ Stereoselectivity in the Darzens Condensation of Substituted Cyclohexanones with (-)-8-Phenylmenthyl α-Chloroacetate

Yoshihiro Shinohara, Yuko Ohba, Ryukichi Takagi, Satoshi Kojima, and Katsuo Ohkata*

*Department of Chemistry, Graduate School of Sciencea, Hiroshima University, 1-3-1 Kagamiyama, Higashi-hiroshima, Hiroshima 739-8526, Japan

Abstract

The Darzens condensation of 4-monosubstituted and cis-3,5-dimethyl-cyclohexanones with (-)-8-phenylmenthyl α-chloroacetate proceeded to give mixtures of trans- and cis-glycidic esters with high enolate face selectivity (>95% de). The presence of axial methyl substituents at the 3 and 5 position lead to decrease in enolate face selectivity. The configuration of the major products was determined by NMR, derivation, and/or X-Ray crystallographic analysis.