Enantioselective Acylation of Silyl Ketene Acetals through Fluoride Anion-Binding Catalysis

descriptionPublicationkeyboard_double_arrow_right Article 10 Aug 2011 United States English Publisher:American Chemical Society (ACS)Journal:Journal of the American Chemical Society, volume 133, pages 13,872-13,875 (issn: 0002-7863, eissn: 1520-5126,

Copyright policy )Funded by:NSERC | unidentified

Authors: Birrell, James Andrew; Desrosiers, Jean-Nicolas; Jacobsen, Eric;

doi: 10.1021/ja205602j

pmid: 21800916

pmc: PMC3164931

Enantioselective Acylation of Silyl Ketene Acetals through Fluoride Anion-Binding Catalysis

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Abstract

A highly enantioselective acylation of silyl ketene acetals with acyl fluorides has been developed to generate useful α,α-disubstituted butyrolactone products. This transformation is promoted by a new thiourea catalyst and 4-pyrrolidinopyridine and represents the first example of enantioselective thiourea anion-binding catalysis with fluoride.

Country

United States

Related Organizations

Harvard University
United States

Keywords

Anions, 570, Acylation, Stereoisomerism, Ethylenes, Ketones, 540, Catalysis, Fluorides, Acetals, 4-Butyrolactone

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