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Issue 16, 2020
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An organocatalytic asymmetric Friedel–Crafts reaction of 2-substituted indoles with aldehydes: enantioselective synthesis of α-hydroxyl ketones by low loading of chiral phosphoric acid

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Abstract

Hydroxyl alkylation of indoles by Friedel–Crafts reaction with a carbonyl compound is a useful strategy. However, the reaction was restricted to ketones due to the easy formation of a bisindole byproduct. Therefore, hydroxyl alkylation of an aldehyde with indole is confronted with great challenges. Here, we report an efficient strategy for asymmetric hydroxyl alkylation of 2-substituted indoles with aldehydes under 0.1 mol% chiral phosphoric acid. A series of α-hydroxyl ketones were obtained in high yields (up to 99%) and good enantioselectivities (up to 97%).

Graphical abstract: An organocatalytic asymmetric Friedel–Crafts reaction of 2-substituted indoles with aldehydes: enantioselective synthesis of α-hydroxyl ketones by low loading of chiral phosphoric acid

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Article information


Submitted
12 Dec 2019
Accepted
22 Jan 2020
First published
22 Jan 2020

Chem. Commun., 2020,56, 2499-2502
Article type
Communication

An organocatalytic asymmetric Friedel–Crafts reaction of 2-substituted indoles with aldehydes: enantioselective synthesis of α-hydroxyl ketones by low loading of chiral phosphoric acid

X. Deng, Y. Wang, S. Zhang, L. Li, G. Li, G. Zhao and Z. Tang, Chem. Commun., 2020, 56, 2499
DOI: 10.1039/C9CC09637J

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