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2007•Journal of the American Chemical SocietyRequires access

Enantioselective Pd-Catalyzed Allylation Reaction of Fluorinated Silyl Enol Ethers

Étienne Bélanger, Katy Cantin, Olivier Messe, Mélanie Tremblay, Jean‐François Paquin

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Abstract

An enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers is reported. This reaction provides a stereoselective and efficient approach to allylated tertiary α-fluoroketones from achiral fluorinated precursors. A variety of cyclic silyl enol ether can be used, and the yields of the desired products range from 52 to 93%, and the enantiomeric excesses range from 83 to 95% ee.

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What this paper is about

An enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers is reported. This reaction provides a stereoselective and efficient approach to allylated tertiary α-fluoroketones from achiral fluorinated precursors. A variety of cyclic silyl enol ether can be used, and the yields of the desired products range from 52 to 93%, and the enantiomeric excesses range from 83 to 95% ee.

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Available abstract

An enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers is reported. This reaction provides a stereoselective and efficient approach to allylated tertiary α-fluoroketones from achiral fluorinated precursors. A variety of cyclic silyl enol ether can be used, and the yields of the desired products range from 52 to 93%, and the enantiomeric excesses range from 83 to 95% ee.

Key concepts: Chemistry, Silylation, Enantioselective synthesis, Enol, Silyl enol ether, Silyl ether, Catalysis, Stereoselectivity

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