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American Chemical Society, Journal of Organic Chemistry, 3(75), p. 589-597, 2009

DOI: 10.1021/jo902120s

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DFT Study on the Factors Determining the Enantioselectivity of Friedel−Crafts Reactions of Indole withN-Acyl andN-Tosylimines Catalyzed by BINOL−Phosphoric Acid Derivatives

Journal article published in 2010 by Luis Simón, Jonathan M. Goodman ORCID
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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Abstract

(Chemical Equation Presented) DFT methods have been used to study the mechanism and the enantioselectivity of the Friedel-Crafts reaction of indoles with acyl and tosyl imides catalyzed by BINOL-phosphoric acid catalysts. The results are in excellent agreement with the experimental enantioselectivities. The energies of the competing transition structures and, thus, the enantioselectivity are rationalized from calculations on a model system. We propose a simple model to predict the absolute configuration of the products.