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Remote stereoselective deconjugation of ?,?-unsaturated esters by simple amidation reactions.

ABSTRACT: The thermodynamically disfavored isomerization of ?,?-unsaturated esters to deconjugated ?,?-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, ?,?-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.

SUBMITTER: Vishe M 

PROVIDER: S-EPMC5664367 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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

Vishe Mahesh M   Hrdina Radim R   Poblador-Bahamonde Amalia I AI   Besnard Céline C   Guénée Laure L   Bürgi Thomas T   Lacour Jérôme J  

Chemical science 20150525 8

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 <i>t</i>BuOK 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, <sup>1</sup>H NMR) irrespective of the size and nature of the  ...[more]

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