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Communication

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

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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

J. Am. Chem. Soc., 2007, 129 (18), pp 5836–5837

DOI: 10.1021/ja071204j

Publication Date (Web): April 14, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mssanfor@umich.edu

Abstract

This report describes a new Pd-catalyzed oxidation reaction for the stereospecific conversion of enynes into cyclopropyl ketones. Unlike related Pd^II/0, Au, and Pt-catalyzed cyclopropane-forming reactions, these transformations proceed with net inversion of geometry with respect to the starting olefin. This result is consistent with a Pd^II/IV mechanism in which the key cyclopropane-forming step involves nucleophilic attack of a tethered olefin onto the Pd^IV−C bond.

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Published In Issue May 09, 2007
Received February 19, 2007

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Communication

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Reactivity of Pd(II) Complexes with Electrophilic Chlorinating Reagents: Isolation of Pd(IV) Products and Observation of C−Cl Bond-Forming Reductive Elimination

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