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Issue 7, 2011
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Chiral phosphoric acid-catalysed Friedel–Crafts alkylation reaction of indoles with racemic spiro indolin-3-ones

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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

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Publication details

The article was received on 28 Mar 2011, accepted on 21 Apr 2011 and first published on 10 May 2011


Article type: Edge Article
DOI: 10.1039/C1SC00190F
Citation: Chem. Sci., 2011,2, 1344-1348
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    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

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