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Issue 17, 2012
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Ketosulfonyl indoles in the regiodefined synthesis of tryptophols and related indole derivatives

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Abstract

Reduction of ketosulfonyl indoles with sodium borohydride provides a ready entry to tryptophols in a regiocomplementary fashion with respect to the traditional oxirane ring-opening by indoles under Friedel–Crafts conditions. Compared to traditional β-ketosulfones, ketosulfonyl indoles show a peculiar behavior since they undergo a Lewis acid promoted elimination of the arylsulfonyl group allowing the preparation of indolyl-substituted 1,4-dicarbonyl derivatives.

Graphical abstract: Ketosulfonyl indoles in the regiodefined synthesis of tryptophols and related indole derivatives

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Publication details

The article was received on 09 Jan 2012, accepted on 29 Feb 2012 and first published on 29 Feb 2012


Article type: Paper
DOI: 10.1039/C2OB25056J
Citation: Org. Biomol. Chem., 2012,10, 3486-3493
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    Ketosulfonyl indoles in the regiodefined synthesis of tryptophols and related indole derivatives

    A. Palmieri and M. Petrini, Org. Biomol. Chem., 2012, 10, 3486
    DOI: 10.1039/C2OB25056J

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