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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: mcquadechem.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 (free Supporting Information)


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