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

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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.

see article for more examples

proposed mechanism

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Key Words

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

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ID: J54-Y2007-1030