Use of Bifunctional Ureas to Increase the Rate of Proline-Catalyzed α-Aminoxylations
Sarah L. Poe, Andrew R. Bogdan, Brian P. Mason, Jeremy L. Steinbacher, Suzanne M. Opalka and D. Tyler McQuade*
*Florida State University, Tallahassee, Florida 32306, Email:
mcquade
chem.fsu.edu
S. L. Poe, A. R. Bogdan, B. P. Mason, J. L. Steinbacher, S. M. Opalka, D. T. McQuade, J. Org. Chem., 2009, 74, 1574-1580.
DOI: 10.1021/jo802461w
Abstract
The rate of the proline-catalyzed α-aminoxylation of aldehydes is significantly increased in the presence of a bifunctional urea originating from the hydrogen bonding interaction between the bifunctional urea and an oxazolidinone intermediate to increase the rate of enamine formation.
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Key Words
Aminoxylations, Organocatalysis
ID: J42-Y2009-0540
