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Highly Chemoselective and Stereoselective Synthesis of Z-Enol Silanes

Ananda Herath and John Montgomery*

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

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

DOI: 10.1021/ja802844v

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A three-component nickel-catalyzed coupling of enals, alkynes, and silanes forms an enol silane and a trisubstituted alkene with >98:2 stereoselectivity. The reaction tolerates a broad range of functionality including aldehydes, ketones, esters, free hydroxyls, and basic secondary amines.

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proposed mechanism

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

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

Catalytic Intermolecular Reductive Coupling of Enones and Alkynes

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

Key Words

Carbonyl Compounds, Silyl Enol Ethers, Alkenes, Multicomponent Reactions, Triethylsilane

ID: J48-Y2008-1730