Synthesis 2018; 50(05): 1039-1046
DOI: 10.1055/s-0036-1591860
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Organocatalytic Friedel–Crafts Hydroxyalkylation of Indoles Using Electrophilic Pyrazole-4,5-diones

Fabrizio Vetica
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Pankaj Chauhan
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Suruchi Mahajan
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Gerhard Raabe
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Received: 08 November 2017

Accepted: 10 November 2017

Publication Date:
07 December 2017 (online)


Abstract

The electrophilic reactivity of a series of novel pyrazole-4,5-dione derivatives in the organocatalytic Friedel–Crafts reaction with various substituted indoles has been tested. The disclosed procedure catalyzed by a cinchona alkaloid derivative allows the conjugation of two very important aza-heterocyclic scaffolds to generate a new class of indolylpyrazolones bearing a tetrasubstituted stereocenter in excellent yields (up to 99%) and with enantioselectivities of up to 94:6 er.

Supporting Information

 
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