Organic Chemistry

Catalytic, Enantioselective α-Alkylation of Azlactones with Non-Conjugated Alkenes via Directed Nucleopalladation

Abstract

A palladium(II)-catalyzed enantioselective α-alkylation of azlactones with non-conjugated alkenes is described. The reaction employs a chiral BINOL-derived phosphoric acid as the source of stereoinduction and a cleavable bidentate directing group appended to the alkene to control regioselectivity and stabilize the nucleopalladated alkylpalladium(II) intermediate in the catalytic cycle. A wide range of azlactones were found to be compatible under the optimal conditions to afford products bearing α,α-disubstituted α-amino acid derivatives with high yields and high enantioselectivity.

Content

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Supplementary material

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Supporting Info
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