title: Catalytic enantioselective protonation of enol trifluoroacetates by means of hydrogenocarbonates and cinchona alkaloids.
abstract: 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.
authors.affiliation: Chimie Organique Bio-organique Réactivité et Analyse, CNRS UMR 6014 & FR 3038, Université et Institut National des Sciences Appliquées (INSA) de Rouen, Rue Tesnière, 76130 Mont-Saint-Aignan, France.
authors.forename: Aurélie
authors.initials: A
authors.lastname: Claraz
authors.forename: Jérôme
authors.initials: J
authors.lastname: Leroy
authors.forename: Sylvain
authors.initials: S
authors.lastname: Oudeyer
authors.forename: Vincent
authors.initials: V
authors.lastname: Levacher
mesh_terms: D000880:Anthraquinones / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D015394:Molecular Structure; D011802:Quinidine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D028561:Transition Elements / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D000880:Anthraquinones; D002930:Cinchona Alkaloids; D028561:Transition Elements; C014486:hydroquinidine; D014269:Trifluoroacetic Acid; D011802:Quinidine