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Issue 33, 2018
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Chemoselective N–H functionalization of indole derivatives via the Reissert-type reaction catalyzed by a chiral phosphoric acid

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Abstract

An asymmetric N-alkylation of indole derivatives via the Reissert-type reaction was realized in the presence of a catalytic amount of chiral phosphoric acid. Various enantioenriched indoles with N-1 substituted by 1,2-dihydroisoquinoline could be obtained under mild conditions in good yields and enantioselectivities at room temperature (up to 98% yield, 94% ee). The current method is compatible with gram-scale reaction and the products can undergo versatile chemical transformations.

Graphical abstract: Chemoselective N–H functionalization of indole derivatives via the Reissert-type reaction catalyzed by a chiral phosphoric acid

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Supplementary files

Article information


Submitted
26 Jun 2018
Accepted
02 Aug 2018
First published
03 Aug 2018

Org. Biomol. Chem., 2018,16, 6146-6154
Article type
Paper

Chemoselective N–H functionalization of indole derivatives via the Reissert-type reaction catalyzed by a chiral phosphoric acid

Y. Cai, Q. Gu and S. You, Org. Biomol. Chem., 2018, 16, 6146
DOI: 10.1039/C8OB01863D

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