He attended Franklin & Marshall College and received his B.A. in Chemistry in 2004. In the Fall of 2004, Andrew entered the graduate program in Chemistry and Chemical Biology at Cornell University and joined the research group of D. Tyler McQuade. His research currently involves the development of microreactors packed with solid-supported catalysts to be used in the continuous processing of small molecules and pharmaceutical agents. Kristin E. Price was born in Baltimore, MD, in 1979. She received her B.A. in Chemistry from Franklin & Marshall College in 2001. In August 2006, she completed her doctoral work under the guidance of Prof. D. Tyler McQuade at Cornell University.
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The rate of the proline-catalyzed alpha-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 enamine formation. Proline derivatives that are incapable of forming oxazolidinones exhibit no rate enhancement in the presence of the bifunctional urea. The rate enhancement is general for a variety of aldehydes, and the faster reactions do not reduce yields or selectivities.
A new strategy for supporting catalysts based on the microencapsulation of linear polymers is presented. In this paper, we present a DMAP capsule that is capable of catalyzing acylation reactions. The catalyst is compared to DMAP on cross-linked and linear polystyrene, as well as small molecule DMAP. Rapid optimization through modification of encapsulation conditions is demonstrated. The optimization provides a dynamic range of catalysis from 90 to 300% of the rate of DMAP on polystyrene.
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