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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

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....

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-02, Vol.56 (16), p.2499-252
Main Authors: Deng, Xiong-fei, Wang, Ying-wei, Zhang, Shi-qi, Li, Ling, Li, Guang-xun, Zhao, Gang, Tang, Zhuo
Format: Article
Language:English
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Summary: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%). Hydroxyl alkylation of indoles by Friedel-Crafts reaction with a carbonyl compound is a useful strategy.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc09637j