This work was supported by the Donors of the Petroleum Research Fund (administered by the American Chemical Society), the Camille and Henry Dreyfus Foundation (New Faculty Award to J.W.B.), and the University of California. K.D.B. was a 2005 DeWolfe Summer Undergraduate Fellow. We are grateful to Joshua Garretson for preliminary efforts.
Chemoselective Amide Ligations by Decarboxylative Condensations of N-Alkylhydroxylamines and α-Ketoacids†
Article first published online: 17 JAN 2006
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 45, Issue 8, pages 1248–1252, February 13, 2006
How to Cite
Bode, J. W., Fox, R. M. and Baucom, K. D. (2006), Chemoselective Amide Ligations by Decarboxylative Condensations of N-Alkylhydroxylamines and α-Ketoacids. Angew. Chem. Int. Ed., 45: 1248–1252. doi: 10.1002/anie.200503991
- Issue published online: 6 FEB 2006
- Article first published online: 17 JAN 2006
- Manuscript Received: 9 NOV 2005
- ligation reactions;
Additive-free: The chemoselective amide-bond-forming ligation between N-alkylhydroxylamines and α-ketoacids requires no reagents and the only by-products are water and carbon dioxide. This process proceeds on unprotected peptide substrates without epimerization, and as such, this process has the potential to serve as a novel chemoselective ligation for the synthesis of peptides and complex materials.