Issue 16, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
23 Dec 2011
Accepted
20 Feb 2012
First published
22 Feb 2012

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

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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