Stereoselective Addition of Carbon-Centered Radicals to Chiral Enamines

Abstract
The reductive alkylation of chiral cyclic enamines via a radical pathway to give 1,2-disubstituted cyclohexanes and 1,2,3,4-tetrahydronaphthalenes containing two new stereogenic centers is described. High diastereoselectivities are observed with enamines prepared from the C 2-symmetric (2R,5R)-2,5-dimethylpyrrolidine. (S)-2-(Methoxymethyl)pyrrolidine also induced good diastereofacialselectivities when the enamines existed exclusively in a cis conformation.

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