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Synthesis of Cyclopropanes via Pd(II/IV)-Catalyzed Reactions of Enynes

Leilani L. Welbes, Thomas W. Lyons, Katie A. Cychosz and Melanie S. Sanford*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, Email: mssanforumich.edu

L. L. Welbes, T. W. Lyons, K. A. Cychosz, M. S. Sanford, J. Am. Chem. Soc., 2007, 129, 5836-5837.

DOI: 10.1021/ja071204j (free Supporting Information)


Abstract

A new Pd-catalyzed oxidation reaction for the stereospecific conversion of enynes into cyclopropyl ketones proceeds with net inversion of geometry with respect to the starting olefin. This result is consistent with a mechanism in which the key cyclopropane-forming step involves nucleophilic attack of a tethered olefin onto the PdIV-C bond.


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Key Words

Cyclopropanes, Lactones, Tetrahydrofurans, Pyrrolidines, y-Lactams, Iodosobenzene Diacetate


ID: J48-Y2007-1600