4.7 Article

Ynamide-Mediated Intermolecular Esterification

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 9, Pages 6188-6194

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00485

Keywords

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Funding

  1. National Natural Science Foundation of China [21778025, 91853114]
  2. Science and Technology Project of Jiangxi Provincial Education Department [GJJ150297]

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An ynamide-mediated one-pot, two-step intermolecular esterification via the condensation of carboxylic acids with nucleophilic hydroxyl species was reported. A broad substrate scope with respect to carboxylic acids, alcohols, and phenols was observed. The alpha-acyloxyenamide intermediates formed by the addition of carboxylic acids to ynamides proved to be effective acylating reagents for the esterification of alcohol and phenol derivatives with the assistance of base catalysis. Notably, the racemization of the alpha-chiral center of carboxylic acids can be avoided.

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