Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis

作者:Foley Megan A; Jamison Timothy F*
来源:Organic Process Research & Development, 2010, 14(5): 1177-1181.
DOI:10.1021/op1001269

摘要

A rapid carboxylic acid-promoted lactone aminolysis is reported. A number of carboxylic acids were found to promote this amide bond-forming transformation, with aliphatic acids being the most efficient. This reaction is an equilibrium process (K(eq) approximate to 1.8), and mechanistic investigations are consistent with mediation of a kinetically important proton-transfer step by the carboxylate, i.e., the conjugate base of the acid employed.

  • 出版日期2010-10