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

ISSN: 1570-1786
E-ISSN: 1875-6255

Diastereoselective Horner-Wadsworth-Emmons Reaction for the Synthesis of Tetrasubstituted Alkenes with an Axis of Chirality
Authors: Shigeki Sano¹, Shinobu Abe², Tomohiro Azetsu³, Michiyasu Nakao⁴, Motoo Shiro⁵ and Yoshimitsu Nagao⁶
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¹ Graduate School of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan. ² Graduate School of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan. ³ Graduate School of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan. ⁴ Graduate School of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan. ⁵ Graduate School of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan. ⁶ Graduate School of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan.
Source: Letters in Organic Chemistry, Volume 3, Issue 11, Nov 2006, p. 798 - 801
DOI: https://doi.org/10.2174/157017806779116969
- Available online: 01 Nov 2006

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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2006-11-01

2025-09-18

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Article Type: Research Article

Keyword(s): asymmetric synthesis; Axis of chirality; diastereoselective; Horner-Wadsworth-Emmons reaction; isomannide; tetrasubstituted alkenes

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

Abstract

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