Copper-Catalyzed Amino Lactonization and Amino Oxygenation of Alkenes Using O‑Benzoylhydroxylamines

A copper-catalyzed amino lactonization of unsaturated carboxylic acids has been achieved as well as the analogous intermolecular three-component amino oxygenation of olefins. The transformation features mild conditions and a remarkably broad substrate scope, offering a novel and efficient approach t...

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Veröffentlicht in:Journal of the American Chemical Society 2016-05, Vol.138 (18), p.5813-5816
Hauptverfasser: Hemric, Brett N, Shen, Kun, Wang, Qiu
Format: Artikel
Sprache:eng
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Zusammenfassung:A copper-catalyzed amino lactonization of unsaturated carboxylic acids has been achieved as well as the analogous intermolecular three-component amino oxygenation of olefins. The transformation features mild conditions and a remarkably broad substrate scope, offering a novel and efficient approach to construct a wide range of amino lactones as well as 1,2-amino alcohol derivatives. Mechanistic studies suggest that the reaction proceeds via a distinctive O-benzoylhydroxylamine-promoted electrophilic amination of alkenes.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b02840