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

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

The Journal of organic chemistry (2011-06-18)
Aurélie Claraz, Jérôme Leroy, Sylvain Oudeyer, Vincent Levacher
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Hydroquinidine hydrochloride, 98%
Sigma-Aldrich
Hydroquinine, 98%