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Issue 8, 2015
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Remote stereoselective deconjugation of α,β-unsaturated esters by simple amidation reactions

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Abstract

The thermodynamically disfavored isomerization of α,β-unsaturated esters to deconjugated β,γ-unsaturated analogues occurs readily when coupled to an amidation. Within the framework of macrocyclic derivatives, it is shown that 15, 16, and 18 membered macrocycles react with tBuOK and anilines to generate, in one-pot, β,γ-unsaturated amides (yields up to 88%). Importantly, single (chiral) diastereomers are isolated (d.r. > 49 : 1, 1H NMR) irrespective of the size and nature of the rings, showing an effective transmission of remote stereochemistry during the isomerization process. CSP-chromatographic resolution and absolute configuration determination by VCD are achieved.

Graphical abstract: Remote stereoselective deconjugation of α,β-unsaturated esters by simple amidation reactions

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Article information


Submitted
27 Mar 2015
Accepted
21 May 2015
First published
25 May 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 4923-4928
Article type
Edge Article

Remote stereoselective deconjugation of α,β-unsaturated esters by simple amidation reactions

M. Vishe, R. Hrdina, A. I. Poblador-Bahamonde, C. Besnard, L. Guénée, T. Bürgi and J. Lacour, Chem. Sci., 2015, 6, 4923
DOI: 10.1039/C5SC01118C

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