A One‐Pot Synthesis of α,β‐Unsaturated Esters From Esters

A convenient method for reductive Horner–Wadsworth–Emmons (HWE) olefination is described. The E‐selective HWE homologation of various esters to α,β‐unsaturated esters was readily achieved and gave the desired products in good‐to‐moderate yields under mild conditions. The one‐pot reaction proceeds th...

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Bibliographic Details
Published in:Bulletin of the Korean Chemical Society 2021, 42(8), , pp.1121-1125
Main Authors: Hong, Chang Whee, Lee, Yong Jin, An, Duk Keun
Format: Article
Language:English
Subjects:
Ester
Horner–Wadsworth–Emmons olefination
Lithium diisobutyl‐t‐butoxyaluminum hydride
Triethyl phosphonoacetate
α,β‐Unsaturated esters
화학
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Summary:A convenient method for reductive Horner–Wadsworth–Emmons (HWE) olefination is described. The E‐selective HWE homologation of various esters to α,β‐unsaturated esters was readily achieved and gave the desired products in good‐to‐moderate yields under mild conditions. The one‐pot reaction proceeds through an in situ generated aldehyde, formed via the partial reduction of an ester with lithium diisobutyl‐t‐butoxyaluminum hydride. The formation of cyclized metal acetal and subsequent decompose to the aldehyde for the olefination was found to be a crucial step in this C2‐carbon homologation protocol. This study demonstrated a one‐pot method for the reductive HWE olefination of esters to α,β‐unsaturated esters with phosphonate carbanion and LDBBA.
ISSN:1229-5949
0253-2964
1229-5949
DOI:10.1002/bkcs.12332