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Rh-Catalyzed Intermolecular Cyclopropanation with α-Alkyl-α-diazoesters: Catalyst-Dependent Chemo- and Diastereoselectivity

Patricia Panne, Andrew DeAngelis and Joseph M. Fox*

*Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, Email: jmfoxudel.edu

P. Panne, A. DeAngelis, J. M. Fox, Org. Lett., 2008, 10, 2987-2989.

DOI: 10.1021/ol800983y (free Supporting Information)


Abstract

In a Rh-catalyzed procedure for the cyclopropanation of alkenes with α-alkyl-α-diazoesters, sterically demanding carboxylate ligands serve to avoid β-hydride elimination. The use of triphenylacetate (TPA) as ligand also imparts high diastereoselectivity.


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Key Words

Cyclopropanation


ID: J54-Y2008-1940