4.8 Article

Regio- and Enantioselective Friedel-Crafts Reactions of Indoles to Epoxides Catalyzed by Graphene Oxide: A Green Approach

Journal

CHEMSUSCHEM
Volume 7, Issue 12, Pages 3279-3283

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201402770

Keywords

carbocatalysis; enantioselectivity; epoxides; graphene oxide; indoles

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Graphene oxide efficiently promotes high regio- and enantio-selective ring opening reactions of aromatic epoxides by indoles addition, in solvent-and metal-free conditions. The Friedel-Crafts products were obtained with enantioselectivity up to 99% ee. The complete inversion of stereochemistry indicates the occurrence of S(N)2-type reaction, which assures high level of enantioselectivity.

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