Issue 17, 2010
From the journal:

Chemical Communications

Squaramide-catalyzed enantioselective Friedel–Crafts reaction of indoles with imines†

Yong Qian,a   Gaoyuan Ma,a   Aifeng Lv,a   Hai-Liang Zhu,a   Jing Zhao*ab  and  Viresh H. Rawal*c  

* Corresponding authors

a State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing, China
E-mail: jingzhao@nju.edu.cn
Fax: +86 25 8359 2672
Tel: +86 25 8359 2672

b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People’s Republic of China

c Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, USA
E-mail: vrawal@uchicago.edu
Tel: +1 773 702 0805

Abstract

Chiral squaramides are highly enantioselective catalysts for Friedel–Crafts reaction of indoles with N-tosyl imines, affording 3-indolyl methanamine products in 85–96% yields and 84–96% ees.

Graphical abstract: Squaramide-catalyzed enantioselective Friedel–Crafts reaction of indoles with imines

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Article information

DOI
https://doi.org/10.1039/B922120D
Article type
Communication
Submitted
22 Oct 2009
Accepted
25 Feb 2010
First published
23 Mar 2010

Chem. Commun., 2010,46, 3004-3006

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Squaramide-catalyzed enantioselective Friedel–Crafts reaction of indoles with imines

Y. Qian, G. Ma, A. Lv, H. Zhu, J. Zhao and V. H. Rawal, Chem. Commun., 2010, 46, 3004 DOI: 10.1039/B922120D

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