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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)


Abstract

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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Allylic Amines via Iridium-Catalyzed C-C Bond Forming Hydrogenation: Imine Vinylation in the Absence of Stoichiometric Byproducts or Metallic Reagents

A. Barchuk, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 8432-8433.


Key Words

Allylic Amines, Hydrogen, Multicomponent Reactions


ID: J48-Y2007-3380