Brønsted Acid-Catalyzed Imine Amidation
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- 21 October 2005
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (45) , 15696-15697
- https://doi.org/10.1021/ja0533085
Abstract
A new method for the Brønsted acid-catalyzed addition of amide nucleophiles to imines to produce protected aminal products is described. Simple Brønsted acids (phenyl phosphinic acid and trifluoromethanesulfonimide) were shown to be excellent catalysts, providing high yields of the aminal product. A catalytic asymmetric imine amidation using sulfonamides as nucleophiles was successful when a hindered biaryl phosphoric acid catalyst derived from 2,2‘-diphenyl-[3,3‘-biphenanthrene]-4,4‘-diol (VAPOL) was used. Excellent yields and enantioselectivities were found in these additions (up to 99% ee).Keywords
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