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Issue 12, 2017
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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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Supplementary files

Article information


Submitted
28 Jul 2017
Accepted
08 Sep 2017
First published
11 Sep 2017

Org. Chem. Front., 2017,4, 2465-2479
Article type
Research Article

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, 4, 2465 DOI: 10.1039/C7QO00649G

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