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An Efficient and General Approach to β-Functionalized Ketones

Jingliang Jiao, Larry X. Nguyen, Dennis R. Patterson and Robert A. Flowers II*

*Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015, Email: rof2lehigh.edu

J. Jiao, L. X. Nguyen, D. R. Patterson, R. A. Flowers II, Org. Lett., 2007, 9, 1323-1326.

DOI: 10.1021/ol070159h (free Supporting Information)


Abstract

A mild oxidation of selected anions (N3-, SCN-, I-, and Br-) by ceric ammonium nitrate (CAN) in the presence of substituted cyclopropyl alcohols provides β-functionalized ketones in short reaction times. This method provides an alternative pathway to important starting materials and intermediates in organic synthesis.


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proposed mechanism



Key Words

cerium(IV) ammonium nitrate, thiocyanates, β-keto azides, β-bromoketones, β-iodoketones, cyclopropanols


ID: J54-Y2007-1030