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Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis.

ABSTRACT: A highly enantioselective acylation of silyl ketene acetals with acyl fluorides has been developed to generate useful ?,?-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.

SUBMITTER: Birrell JA 

PROVIDER: S-EPMC3164931 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis.

Birrell James A JA   Desrosiers Jean-Nicolas JN   Jacobsen Eric N EN  

Journal of the American Chemical Society 20110810 35

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. ...[more]

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