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Issue 10, 2017
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Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters

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Abstract

This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate from the easily accessible γ-hydroxy-α,β-alkenoic ester. The in situ generated dienolate can react with benzaldehyde and undergo a practical, useful tandem allylic isomerization-Aldol reaction to afford more functionalized compounds.

Graphical abstract: Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters

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Article information


Submitted
18 Jan 2017
Accepted
13 Feb 2017
First published
13 Feb 2017

Org. Biomol. Chem., 2017,15, 2185-2190
Article type
Paper

Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters

L. Lai, A. Li, J. Zhou, Y. Guo, L. Lin, W. Chen and R. Wang, Org. Biomol. Chem., 2017, 15, 2185
DOI: 10.1039/C7OB00131B

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