Ynamide-Mediated Intermolecular Esterification
Xuewei Wang, Yang Yang, Yongli Zhao, Sheng Wang, Wenchang Hu, Jin Li, Zihao Wang, Feng‐Ling Yang, Junfeng Zhao
Abstract
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 α-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 α-chiral center of carboxylic acids can be avoided.
Topics & Concepts
ChemistryRacemizationNucleophileAlcoholOrganic chemistryPhenolPhenolsCatalysisReagentIntermolecular forceSubstrate (aquarium)Carboxylic acidCombinatorial chemistryMoleculeGeologyOceanographyCatalytic Alkyne ReactionsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods