Issue 23, 2010
From the journal:

Chemical Communications

Enantioselective Friedel–Crafts alkylation reaction of indoles with α,β-unsaturated acyl phosphonates catalyzed by chiral phosphoric acid†

Prabhakar Bachua  and  Takahiko Akiyama*a  

* Corresponding authors

a Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan
E-mail: takahiko.akiyama@gakushuin.ac.jp
Fax: +81 3 5992 1029
Tel: +81 3 3986 0221

Abstract

A variety of indoles underwent enantioselective Friedel–Crafts alkylation with α,β-unsaturated acyl phosphonates in the presence of 10 mol% chiral BINOL-based phosphoric acid and subsequent treatment with methanol and DBU to give methyl 3-(indol-3-yl)propanoates in good yields and with high enantioselectivities.

Graphical abstract: Enantioselective Friedel–Crafts alkylation reaction of indoles with α,β-unsaturated acyl phosphonates catalyzed by chiral phosphoric acid

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Article information

DOI
https://doi.org/10.1039/C000862A
Article type
Communication
Submitted
15 Jan 2010
Accepted
12 Feb 2010
First published
16 Mar 2010

Chem. Commun., 2010,46, 4112-4114

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Enantioselective Friedel–Crafts alkylation reaction of indoles with α,β-unsaturated acyl phosphonates catalyzed by chiral phosphoric acid

P. Bachu and T. Akiyama, Chem. Commun., 2010, 46, 4112 DOI: 10.1039/C000862A

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