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Synlett 1990; 1990(10): 624-626
DOI: 10.1055/s-1990-21190
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Stereoselective Addition of Carbon-Centered Radicals to Chiral Enamines

Philippe Renaud* , Serge Schubert
  • *Institut de Chimie Organique, Université de Lausanne, 2 Rue de la Barre, CH-1005 Lausanne, Switzerland
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Publication Date:
08 March 2002 (online)

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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.