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A Rh-catalyzed procedure for the cyclopropanation of alkenes with alpha-alkyl-alpha-diazoesters is described. With dirhodium tetraoctanoate, the predominant pathway is beta-hydride elimination. While a number of sterically demanding carboxylate ligands serve to avoid beta-hydride elimination, it was found that triphenylacetate (TPA) also imparts high diastereoselectivity.

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