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Computational Predictions of Stereochemistry in Asymmetric Thiazolium- and Triazolium-Catalyzed Benzoin Condensations

Travis Dudding, Kendall N. Houk and Barry M. Trost
Proceedings of the National Academy of Sciences of the United States of America
Vol. 101, No. 16 (Apr. 20, 2004), pp. 5770-5775
Stable URL: http://www.jstor.org/stable/3371911
Page Count: 6
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Since scans are not currently available to screen readers, please contact JSTOR User Support for access. We'll provide a PDF copy for your screen reader.
Computational Predictions of Stereochemistry in Asymmetric Thiazolium- and Triazolium-Catalyzed Benzoin Condensations
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Abstract

The catalytic asymmetric thiazolium- and triazolium-catalyzed benzoin condensations of aldehydes and ketones were studied with computational methods. Transition-state geometries were optimized by using Morokuma's IMOMO [integrated MO (molecular orbital) + MO method] variation of ONIOM (n-layered integrated molecular orbital method) with a combination of B3LYP/6-31G(d) and AM1 levels of theory, and final transition-state energies were computed with single-point B3LYP/6-31G(d) calculations. Correlations between experiment and theory were found, and the origins of stereoselection were identified. Thiazolium catalysts were predicted to be less selective then triazolium catalysts, a trend also found experimentally.

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