Scientific article
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English

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

Published inChemical science, vol. 6, no. 8, p. 4923-4928
Publication date2015
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.

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Citation (ISO format)
VISHE, Mahesh et al. Remote stereoselective deconjugation of α,β-unsaturated esters by simple amidation reactions. In: Chemical science, 2015, vol. 6, n° 8, p. 4923–4928. doi: 10.1039/C5SC01118C
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ISSN of the journal2041-6520
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Creation07/15/2015 5:06:00 PM
First validation07/15/2015 5:06:00 PM
Update time03/14/2023 11:28:25 PM
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