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Efficient Transfer of Chelating Amides into Different Types of Esters and Lactones
Author(s) -
Jakob Uwe,
Mundinger Stephan,
Bannwarth Willi
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402843
Subject(s) - chemistry , chelation , nucleophile , amide , organic chemistry , nucleophilic addition , carboxylic acid , combinatorial chemistry , catalysis
We describe a general and versatile approach for the conversion of carboxylic acid amides into their corresponding esters despite the fact that the former are thermodynamically more stable. The transformations are mediated by the coordination of Cu I by a chelating entity. The resulting weakening of the amide bond allows for nucleophilic attack by alcoholic hydroxyl functions. The principle is demonstrated for a wide variety of transformations, leading to different kinds of esters and lactones.