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Synfacts 2008(2): 0159-0159  
DOI: 10.1055/s-2007-992487
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Enantioselective Alkyne-Imine Reductive Coupling

Contributor(s): Mark Lautens, Praew Thansandote
M.-Y. Ngai, A. Barchuk, M. J. Krische*
University of Texas at Austin, USA
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

This paper demonstrates the first catalytic enantioselective alkyne-imine reductive coupling which the authors use to devise a convenient route for synthesizing optically enriched allylic amines. An advantage of this approach is the absence of stoichiometric byproducts. The scope is very broad with excellent yields and enantioselectivies for a wide variety of alkynes and N-arylsulfonyl imines.