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Catalytic asymmetric C2-nucleophilic substitutions of C3-substituted indoles with ortho-hydroxybenzyl alcohols

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Abstract

Catalytic asymmetric C2-nucleophilic substitutions of C3-substituted indoles such as tryptophols and tryptamines with ortho-hydroxybenzyl alcohols have been established, leading to the generation of triaryl methane products in generally high yields and excellent enantioselectivities (up to 99% yield, 98% ee). This class of C2-nucleophilic substitutions has wide substrate scope, which is not only applicable to a wide range of ortho-hydroxybenzyl alcohols, but also amenable to various tryptophols, tryptamines and other C3-substituted indoles. In addition, the reaction could be scaled up with maintained yield and enantioselectivity.

Graphical abstract: Catalytic asymmetric C2-nucleophilic substitutions of C3-substituted indoles with ortho-hydroxybenzyl alcohols

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Publication details

The article was received on 28 Jul 2017, accepted on 08 Sep 2017 and first published on 11 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00649G
Citation: Org. Chem. Front., 2017, Advance Article
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    Catalytic asymmetric C2-nucleophilic substitutions of C3-substituted indoles with ortho-hydroxybenzyl alcohols

    J. Wu, J. Wang, P. Wu, G. Mei and F. Shi, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00649G

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