Diastereoselective Horner-Wadsworth-Emmons Reaction for the Synthesis of Tetrasubstituted Alkenes with an Axis of Chirality

Shigeki      Sano; Shinobu      Abe; Tomohiro      Azetsu; Michiyasu      Nakao; Motoo      Shiro; Yoshimitsu      Nagao

doi:10.2174/157017806779116969

Abstract

An asymmetric Horner-Wadsworth-Emmons (HWE) reaction of σ-symmetric 4-methylcyclohexanone (6c) and a novel HWE reagent 4a bearing O-benzylisomannide was investigated by employing Sn(OSO2CF3)2 and N-ethylpiperidine. As a result, α-methyl-a,β-unsaturated ester 7c, a tetrasubstituted alkene with an axis of chirality, was obtained in > 99% de.

Keywords: Axis of chirality, Horner-Wadsworth-Emmons reaction, asymmetric synthesis, isomannide, tetrasubstituted, alkenes, diastereoselective

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Letters in Organic Chemistry

Title: Diastereoselective Horner-Wadsworth-Emmons Reaction for the Synthesis of Tetrasubstituted Alkenes with an Axis of Chirality

Volume: 3 Issue: 11

Author(s): Shigeki Sano, Shinobu Abe, Tomohiro Azetsu, Michiyasu Nakao, Motoo Shiro and Yoshimitsu Nagao

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Keywords: Axis of chirality, Horner-Wadsworth-Emmons reaction, asymmetric synthesis, isomannide, tetrasubstituted, alkenes, diastereoselective

Abstract: An asymmetric Horner-Wadsworth-Emmons (HWE) reaction of σ-symmetric 4-methylcyclohexanone (6c) and a novel HWE reagent 4a bearing O-benzylisomannide was investigated by employing Sn(OSO2CF3)2 and N-ethylpiperidine. As a result, α-methyl-a,β-unsaturated ester 7c, a tetrasubstituted alkene with an axis of chirality, was obtained in > 99% de.

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Sano Shigeki, Abe Shinobu, Azetsu Tomohiro, Nakao Michiyasu, Shiro Motoo and Nagao Yoshimitsu, Diastereoselective Horner-Wadsworth-Emmons Reaction for the Synthesis of Tetrasubstituted Alkenes with an Axis of Chirality, Letters in Organic Chemistry 2006; 3 (11) . https://dx.doi.org/10.2174/157017806779116969