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Synfacts 2005(3): 0307-0307  
DOI: 10.1055/s-2005-916129
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

‘Open-Flask’ Enantioselective Reduction of Ketimines

Contributor(s): Mark Lautens, Andrew Martins
K. A. Nolin, R. W. Ahn, F. D. Toste*
University of California, Berkeley, USA
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

Under ‘open-flask’ conditions, in the presence of a Re(V) complex and silane, N-substituted ketimines can be converted into secondary amines with high enantiomeric excess. In general, yields and enantioselectivities are high, with both imine and enamine tautomers affording product. The method was extended to the synthesis of phenylglycine derivatives with no detectable racemization, and α,β-unsaturated imines could be converted into allylamines with high ee.