Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis
Author(s)Foley, Megan A.; Jamison, Timothy F.
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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[subscript eq] ≈ 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.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Organic Process Research & Development
American Chemical Society (ACS)
Foley, Megan A., and Timothy F. Jamison. “Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis.” Organic Process Research & Development 14.5 (2010): 1177–1181.
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