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N-Heterocyclic Carbene-Catalyzed Conjugate Additions of Alcohols

Eric M. Phillips, Matthias Riedrich and Karl A. Scheidt*

*Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Silverman Hall, 2145 Sheridan Road, Evanston, Illinois 60208, Email: scheidtnorthwestern.edu

E. M. Phillips, M. Riedrich, K. A. Scheidt, J. Am. Chem. Soc., 2010, 132, 13179-13181.

DOI: 10.1021/ja1061196 (free Supporting Information)


Abstract

An efficient intermolecular conjugate addition of various primary and secondary alcohols to unsaturated ketones and esters is catalyzed by the free carbene derived from IMes·HCl. No oligomerization is observed under these mild conditions. In addition to reactions with activated alkenes, IMes catalyzes the formation of vinyl ethers through the 1,4-addition of alcohols to ynones.

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Key Words

ethers, conjugate addition


ID: J48-Y2010-2630