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Synfacts 2011(6): 0646-0646  
DOI: 10.1055/s-0030-1260387
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Propargylation of Imines

Contributor(s): Mark Lautens, Stephen G. Newman
H. M. Wisniewska, E. R. Jarvo*
University of California, Irvine, USA
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

Propargylation reactions give access to useful chiral products with orthogonal functional groups. The authors have developed the first catalytic asymmetric propargylation of ­imines to provide homoallylic amines in good yields and enantioselectivity. An allenyl boron nucleophile is used, which may act as either a propargyl or an allenyl nucleophile. By using Walphos ligands, only propargylated products are observed.