Publication:
Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts alkylation of indoles with γ-hydroxy-γ-lactams

Issued Date

2013-03-25

Resource Type

Article

ISSN

16154169
16154150

DOI

10.1002/adsc.201201008

Other identifier(s)

2-s2.0-84875458564

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Advanced Synthesis and Catalysis. Vol.355, No.5 (2013), 836-840

Suggested Citation

Thibaut Courant, Sirirat Kumarn, Long He, Pascal Retailleau, Géraldine Masson Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts alkylation of indoles with γ-hydroxy-γ-lactams. Advanced Synthesis and Catalysis. Vol.355, No.5 (2013), 836-840. doi:10.1002/adsc.201201008 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/31483

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Title

Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts alkylation of indoles with γ-hydroxy-γ-lactams

Author(s)

Thibaut Courant
 Sirirat Kumarn
 Long He
 Pascal Retailleau
 Géraldine Masson

Other Contributor(s)

Institut de Chimie des Substances Naturelles
 Chulabhorn Research Institute
 Mahidol University

Abstract

An enantioselective aza-Friedel-Crafts reaction of indoles with γ-hydroxy-γ-lactams using a chiral phosphoric acid catalyst is reported. The approach described herein provides an efficient access to 5-indolylpyrrolidinones in good to quantitative yields and excellent enantioselectivities (up to >99% ee). The results suggest that the reaction may proceed via N-acyliminium intermediates associated with the chiral phosphoric acid anion. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keyword(s)

Chemical Engineering
 Chemistry

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/31483

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Scopus 2011-2015