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  • Title: DFT study on the factors determining the enantioselectivity of Friedel-Crafts reactions of indole with N-acyl and N-tosylimines catalyzed by BINOL-phosphoric acid derivatives.
    Author: Simón L, Goodman JM.
    Journal: J Org Chem; 2010 Feb 05; 75(3):589-97. PubMed ID: 20039624.
    Abstract:
    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.
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