Issue 16, 2012
From the journal:

Organic & Biomolecular Chemistry

Enantioselective synthesis of fluorene derivatives by chiral N-triflyl phosphoramide catalyzed double Friedel–Crafts alkylation reaction†‡

Shou-Guo Wang,a   Long Han,a   Mi Zeng,a   Feng-Lai Sun,a   Wei Zhanga  and  Shu-Li You*a  

* Corresponding authors

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Lu, Shanghai, China
E-mail: slyou@sioc.ac.cn
Fax: (+86) 21-54925087

Abstract

A highly efficient tandem double Friedel–Crafts reaction between indoles and 2-formylbiphenyl derivatives by chiral N-triflyl phosphoramide was realized. Under mild conditions, various 9-(3-indolyl) fluorene derivatives have been obtained in good yield and up to 94% ee. Comparing to their corresponding chiral phosphoric acids, chiral N-triflyl phosphoramides catalyzed reactions led to products with opposite absolute configuration.

Graphical abstract: Enantioselective synthesis of fluorene derivatives by chiral N-triflyl phosphoramide catalyzed double Friedel–Crafts alkylation reaction

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Article information

DOI
https://doi.org/10.1039/C2OB07168A
Article type
Paper
Submitted
23 Dec 2011
Accepted
20 Feb 2012
First published
22 Feb 2012

Org. Biomol. Chem., 2012,10, 3202-3209

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Enantioselective synthesis of fluorene derivatives by chiral N-triflyl phosphoramide catalyzed double Friedel–Crafts alkylation reaction

S. Wang, L. Han, M. Zeng, F. Sun, W. Zhang and S. You, Org. Biomol. Chem., 2012, 10, 3202 DOI: 10.1039/C2OB07168A

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