Issue 16, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
12 Dec 2019
Accepted
22 Jan 2020
First published
22 Jan 2020

Chem. Commun., 2020,56, 2499-2502

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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