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Issue 16, 2012
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Enantioselective synthesis of fluorene derivatives by chiral N-triflyl phosphoramide catalyzed double Friedel–Crafts alkylation reaction

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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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Publication details

The article was received on 23 Dec 2011, accepted on 20 Feb 2012 and first published on 22 Feb 2012


Article type: Paper
DOI: 10.1039/C2OB07168A
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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