Journal
TETRAHEDRON
Volume 65, Issue 16, Pages 3211-3221Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.10.107
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Funding
- NIGMS NIH HHS [R01 GM073836-03, R01 GM073836-01, R01 GM073836-04, R01 GM073836, R01 GM073836-02] Funding Source: Medline
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This report describes detailed studies of the scope and mechanism of a new Pd-catalyzed oxidation reaction for the stereospecific conversion of enynes into cyclopropyl ketones. Unlike related Pd-II/O, Au and Pt-catalyzed cyclopropane-forming reactions, these transformations proceed with net inversion of geometry with respect to the starting alkene. This result, along with other mechanistic data, is consistent with a Pd-II/IV mechanism in which the key cycloptopane-forming step involves nucleophilic attack of a tethered olefin onto a Pd-IV-C bond. (C) 2008 Elsevier Ltd. All rights reserved.
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