Use of bifunctional ureas to increase the rate of proline-catalyzed α-aminoxylations

…, AR Bogdan, BP Mason, JL Steinbacher…

Index: Poe, Sarah L.; Bogdan, Andrew R.; Mason, Brian P.; Steinbacher, Jeremy L.; Opalka, Suzanne M.; Tyler McQuade Journal of Organic Chemistry, 2009 , vol. 74, # 4 p. 1574 - 1580

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Citation Number: 40

Abstract

The rate of the proline-catalyzed α-aminoxylation of aldehydes is significantly increased in the presence of a bifunctional urea. Structure− activity relationship data indicate that both an amine and a urea are crucial for rate enhancement. The evidence presented herein suggests that this rate enhancement originates from the hydrogen bonding interaction between the bifunctional urea and an oxazolidinone intermediate to increase the rate of ...