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Evolution of Efficient Strategies for Enone-Alkyne and Enal-Alkyne Reductive Couplings

Wei Li, Ananda Herath and John Montgomery*

*Department of Chemistry, 930 North University Avenue, University of Michigan, Ann Arbor, Michigan 48109-1055, Email:

W. Li, A. Herath, J. Montgomery, J. Am. Chem. Soc., 2009, 131, 17024-17029.

DOI: 10.1021/ja9083607

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Reductive coupling of enones or enals with alkynes using reducing agents such as organozincs, organoboranes, organosilanes, and methanol is cost-effective, and tolerant of many functional groups. Isotopic labeling strategies have provided supporting evidence for the mechanistic proposals.

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Catalytic Intermolecular Reductive Coupling of Enones and Alkynes

A. Herath, B. B. Thompson, J. Montgomery, J. Am. Chem. Soc., 2007, 129, 8712-8713.

Highly Chemoselective and Stereoselective Synthesis of Z-Enol Silanes

A. Herath, J. Montgomery, J. Am. Chem. Soc., 2008, 130, 8132-8133.

Key Words

Alkenes, Carbonyl Compounds

ID: J48-Y2009-3400