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Synfacts 2008(7): 0738-0738  
DOI: 10.1055/s-2008-1078464
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Domino Stereoselective Cross-Metathesis-Imine Cinnamylation

Contributor(s): Mark Lautens, Praew Thansandote
J. D. Huber, N. R. Perl, J. L. Leighton*
Columbia University, New York, USA
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Publication History

Publication Date:
20 June 2008 (online)

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Significance

A one-pot domino cross-meta­thesis/imine allylation gives a useful alternative to multi-step syntheses of homoallylic amines. By using a chiral allylsilane, the amine products are produced in high diastereoselectivities and enan­tioselectivities. A three-step, one-pot procedure has also been developed to make substituted piperidines.