Catalytic enantioselective protonation of enol trifluoroacetates by means of hydrogenocarbonates and cinchona alkaloids. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2011

Catalytic enantioselective protonation of enol trifluoroacetates by means of hydrogenocarbonates and cinchona alkaloids.

Résumé

Herein is disclosed an efficient catalytic enantioselective protonation of enol acetates by means of a readily implementable transition-metal-free chemical process. By making use of simple hygrogenocarbonates as the proton source and hydroquinine anthraquinone-1,4-diyl diether as the chiral proton shuttle, a series of cyclic enol trifluoroacetates are protonated under mild conditions to yield the corresponding ketones in up to 93% ee.

Domaines

Chimie organique
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Dates et versions

hal-00992157 , version 1 (16-05-2014)

Identifiants

Citer

Aurélie Claraz, Jérôme Leroy, Sylvain Oudeyer, Vincent Levacher. Catalytic enantioselective protonation of enol trifluoroacetates by means of hydrogenocarbonates and cinchona alkaloids.. Journal of Organic Chemistry, 2011, 76 (15), pp.6457-6463. ⟨10.1021/jo201146b⟩. ⟨hal-00992157⟩
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