Ambiphilic Reactivity of Vinyl Pd-Oxyallyl for Expeditious Construction of Highly Functionalized Cyclooctanoids
- 10 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (19), 7330-7335
- https://doi.org/10.1021/acs.orglett.1c02401
Abstract
We report the catalytic generation of a vinyl Pd-oxyallyl that dimerizes regiospecifically to form highly functionalized nonbridged cyclooctanoids. Such compounds are otherwise synthetically challenging, but highly useful in synthesis. This vinyl Pd-oxyallyl species demonstrates both electrophilic and nucleophilic properties. DFT calculations elucidate the mechanism and the origins of the chemoselective cyclooctanoid formation.Keywords
Funding Information
- National Science Foundation (CHE-1764328)
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