Enantioselective Reductive Coupling of Acetylene to N-Arylsulfonyl Imines via Rhodium Catalyzed C-C Bond-Forming Hydrogenation: (Z)-Dienyl Allylic Amines

Eduardas Skucas, Jong Rock Kong and Michael J. Krische*

*Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, Email: mkrischemail.utexas.edu

E. Skucas, J. R. Kong, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 7242-7243.

DOI: 10.1021/ja0715896

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Abstract

Exposure of aromatic and aliphatic N-arylsulfonyl aldimines to equal volumes of acetylene and hydrogen gas at 45°C and ambient pressure in the presence of chirally modified cationic rhodium catalysts provides (Z)-dienyl allylic amines in highly optically enriched form and as single geometrical isomers.

see article for more examples

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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.

Catalytic Carbonyl Z-Dienylation via Multicomponent Reductive Coupling of Acetylene to Aldehydes and α-Ketoesters Mediated by Hydrogen: Carbonyl Insertion into Cationic Rhodacyclopentadienes

J. R. Kong, M. J. Krische, J. Am. Chem. Soc., 2006, 128, 16040-16041.

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Key Words

Allylic Amines, Dienes, Multicomponent Reactions, Hydrogen

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ID: J48-Y2007-1810