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Facile Synthesis of Z-Alkenes via Uphill Catalysis

Kamaljeet Singh, Shannon J. Staig and Jimmie D. Weaver*

*Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078, United States, Email: Jimmie.weaverokstate.edu

K. Singh, S. J. Staig, J. D. Weaver, J. Am. Chem. Soc., 2014, 136, 5275-5278.

DOI: 10.1021/ja5019749 (free Supporting Information)


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Abstract

Catalytic access to thermodynamically less stable Z-alkenes have relied upon kinetic control of the reaction. A mild and simple orthogonal approach proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer via a photochemical pumping mechanism.

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Key Words

isomerizations, Z-alkenes, allylic amines, allylic alcohols


ID: J48-Y2014