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Iridium-Catalyzed C-C Bond Forming Hydrogenation: Direct Regioselective Reductive Coupling of Alkyl-Substituted Alkynes to Activated Ketones

Ming-Yu Ngai, Andriy Barchuk and Michael J. Krische*

*Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, Email:

M.-Y. Ngai, A. Barchuk, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 280-281.

DOI: 10.1021/ja0670815


An iridium-catalyzed, hydrogen-mediated reductive C-C bond formation of alkynes in the presence of α-ketoesters affords β,γ-unsaturated α-hydroxyesters in excellent yield, with complete control of olefin geometry and, in most cases, with excellent regiocontrol.

see article for more examples

Highly Enantioselective Direct Reductive Coupling of Conjugated Alkynes and α-Ketoesters via Rhodium-Catalyzed Asymmetric Hydrogenation

J.-R. Kong, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc., 2006, 128, 718-719.

Key Words

Allylic Alcohols, Hydrogen

ID: J48-Y2007-0030