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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: mkrischemail.utexas.edu

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

DOI: 10.1021/ja0670815 (free Supporting Information)


Abstract

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.

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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