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Synfacts 2006(5): 0461-0461  
DOI: 10.1055/s-2006-934359
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Highly Enantioselective Meerwein-Schmidt-Ponndorf-Verley Reduction of Ketimines

Contributor(s): Mark Lautens, Frédéric Ménard
C. R. Graves, K. A. Scheidt*, S. T. Nguyen*
Northwestern University, Evanston, USA
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

The asymmetric Meerwein-Schmidt-Ponndorf-Verley (MSPV) reduction of N-phosphinoylketimines using an inexpensive metal and a readily available chiral ligand was ­developed. A wide range of structurally diverse N-phosphinoylimines was reduced (10 examples). Remarkably, primary alkyl groups can be distinguished and even substrates bearing n-pentyl vs. ethyl were converted into amine 3 with impressive stereocontrol. The model proposed to predict the absolute configuration of the products is supported by NMR studies.