Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 18, Pages 5836-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja071204j
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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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