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

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2011

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American Chemical Society
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Birrell, James A., Jean-Nicolas Desrosiers, and Eric N. Jacobsen. 2011. Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis. Journal of the American Chemical Society 133(35): 13872 -13875.

Abstract

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

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