Issue 24, 2012
From the journal:

Organic & Biomolecular Chemistry

Asymmetric Friedel–Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes†

Yang Jia,a   Wen Yanga  and  Da-Ming Du*a  

* Corresponding authors

a School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
E-mail: dudm@bit.edu.cn
Tel: +86 10 68914985

Abstract

An efficient diastereo- and enantioselective Friedel–Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes has been developed. This asymmetric Friedel–Crafts alkylation led to medicinally privileged indolyl(nitro)chromans in good yields with high enantioselectivities (up to 95% ee) and diastereoselectivities under mild reaction conditions.

Graphical abstract: Asymmetric Friedel–Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes

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Article information

DOI
https://doi.org/10.1039/C2OB25360G
Article type
Paper
Submitted
20 Feb 2012
Accepted
20 Apr 2012
First published
25 Apr 2012

Org. Biomol. Chem., 2012,10, 4739-4746

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Asymmetric Friedel–Crafts alkylation of indoles with 3-nitro-2H-chromenes catalyzed by diphenylamine-linked bis(oxazoline) and bis(thiazoline) Zn(II) complexes

Y. Jia, W. Yang and D. Du, Org. Biomol. Chem., 2012, 10, 4739 DOI: 10.1039/C2OB25360G

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