Issue 7, 2011
From the journal:

Chemical Science

Chiral phosphoric acid-catalysed Friedel–Crafts alkylation reaction of indoles with racemic spiro indolin-3-ones†

Qin Yina  and  Shu-Li You*a  

* Corresponding authors

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, China
E-mail: slyou@sioc.ac.cn
Fax: (+86) 21-5492-5087

Abstract

Chiral phosphoric acid-catalysed Friedel–Crafts alkylation reactions of indoles, pyrrole and 3-(dimethylamino)phenol with racemic spiro indolin-3-ones have been realised. With 5 mol% (S)-TRIP, Friedel–Crafts adducts bearing a quaternary stereocentre were obtained in up to 99% yield and 99% ee. The reaction features readily available, stable starting materials and delivers synthetically useful but challenging products.

Graphical abstract: Chiral phosphoric acid-catalysed Friedel–Crafts alkylation reaction of indoles with racemic spiro indolin-3-ones

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1SC00190F
Article type
Edge Article
Submitted
28 Mar 2011
Accepted
21 Apr 2011
First published
10 May 2011

Chem. Sci., 2011,2, 1344-1348

Permissions

Request permissions

Chiral phosphoric acid-catalysed Friedel–Crafts alkylation reaction of indoles with racemic spiro indolin-3-ones

Q. Yin and S. You, Chem. Sci., 2011, 2, 1344 DOI: 10.1039/C1SC00190F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements