Enantioselective Iridium-Catalyzed Imine Vinylation: Optically Enriched Allylic Amines via Alkyne−Imine Reductive Coupling Mediated by Hydrogen
Ming-Yu Ngai , Andriy Barchuk and Michael J. Krische*
*Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, Email: mkrischemail.utexas.edu
M.-Y. Ngai, A. Barchuk, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 12644-12645.
DOI: 10.1021/ja075438e (free Supporting Information)
Using an iridium catalyst modified by (R)-Cl,MeO-BIPHEP, the hydrogenating of alkynes in the presence of N-arylsulfonyl imines delivers the corresponding allylic amines in highly optically enriched form. This protocol circumvents the use of preformed vinyl metal reagents and is applicable to aromatic, heteroaromatic, and aliphatic N-arylsulfonyl aldimines.
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A. Barchuk, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 8432-8433.