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Issue 8, 2015
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Chiral Brønsted acid-catalyzed Friedel–Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes

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Abstract

We disclose herein a highly enantioselective protocol for the Brønsted acid-catalyzed addition of indoles and phenols to in situ-generated ortho-quinone methides which deliver broadly substituted diarylindolylmethanes and triarylmethanes, respectively, in a one-pot reaction under very mild conditions. A chiral phosphoric acid catalyst has been developed for this process serving to convert the starting ortho-hydroxybenzhydryl alcohols into the reactive ortho-quinone methides and to control the enantioselectivity of the carbon–carbon bond-forming event via hydrogen-bonding.

Graphical abstract: Chiral Brønsted acid-catalyzed Friedel–Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes

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Publication details

The article was received on 29 Oct 2014, accepted on 02 Dec 2014 and first published on 03 Dec 2014


Article type: Communication
DOI: 10.1039/C4CC08559K
Chem. Commun., 2015,51, 1461-1464
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    Chiral Brønsted acid-catalyzed Friedel–Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes

    S. Saha, S. K. Alamsetti and C. Schneider, Chem. Commun., 2015, 51, 1461
    DOI: 10.1039/C4CC08559K

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