Amide Bond Formation via Reversible, Carboxylic Acid-Promoted Lactone Aminolysis
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MAF TFJ OPRD 2010.pdf
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391.45 KB
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Author(s)
Foley, Megan A.
Jamison, Timothy F.
Date Issued
August 2010
Journal
Organic Process Research & Development
Publisher
American Chemical Society (ACS)
Citation
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.
Version
Author's final manuscript
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/op1001269
