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George Negrete

Asst. Prof. of Chemistry
Division of Earth & Physical Sciences
University of Texas at San Antonio
6900 N. Loop 1604 W.
San Antonio, TX 78249-0663

Phone: (210) 458-5448
FAX: (210) 458-4469
Email: gnegrete@utsa.edu



B.S. Stanford University 1984
Ph.D. University of California, Santa Cruz 1990


Description of Research
We are investigating the properties of pi-stacking interactions and their application in stereoselective synthetic methods. We are investigating a new, kinetic resolution of racemic aryl epoxides via nucleophilic opening with chiral carboxylic acids and amines. This project is based on the hypothesis that a previously observed diastereoselective epoxide opening with an enantiomerically pure carboxylic acid results from complementary pi-stacking and steric interactions. A rationally implemented amplification of the diastereoselectivity is proposed as the basis for the kinetic resolution of the epoxide. This methodology targets the preparation of carcinogen metabolite intermediates and is supported by the National Institutes of Health. We are also engaged in a research program on the design of non-covalently bound templates for the asymmetric functionalization of achiral substrates. The target complexes are bound by pi-stacking and either hydrogen-bonding or ionic interactions. This work is supported by The Welch Foundation.
Recent Papers or Publications
Vincent A. Boyd, Yousuf P. Najjar, Larry A. Ytuarte, Michael M. Savage, Joe B. Perales, Thomas Meehan and George R. Negrete "Complementary Approaches to the Preparations of Cis and Trans Aminohydrins," Tetrahedron Lett. 1998, 39, 3459-3462.

Vincent A. Boyd, Joe B. Perales, and George R. Negrete "Design and Implementation of New Auxiliaries for Asymmetric Enolate Alkylations," Tetrahedron Lett. 1997, 38, 6631-6634.

Alan R. Wolfe, George R. Negrete, Thomas Meehan, and Qi Song "Benzo[a]pyrene Diol Epoxide-DNA Cis Adduct Formation Through a Trans Chlorohydrin Intermediate," Proc. Natl. Acad. Sci. USA 1997, 94, 1749-1754.

Special Honors or Awards
UTSA Alumni Association Distinguished Faculty Teaching Award (1997)

National Institutes of Health Postdoctoral Fellow (1992)

UC President's Dissertation Year Fellow (1988)

Patricia Roberts Harris Fellow (1984-7)

UC Regents' Fellow (1984)

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