Rhodium(I)-Catalyzed Direct Enantioselective C–H Functionalization of Indoles

A highly regiospecific vinylogous carbene insertion protocol for direct asymmetric C–H functionalization of indoles with arylvinyldiazoacetates has been developed. Under the catalysis of simple Rh­(I)/chiral diene complexes, the reaction occurs solely at the vinylogous position of the vinylcarbenoid...

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Published in:Journal of organic chemistry 2023-06, Vol.88 (12), p.7844-7848
Main Authors: Zhu, Dong-Xing, Xu, Ming-Hua
Format: Article
Language:English
Subjects:
Catalysis
Indoles
Polyenes
Rhodium
Stereoisomerism
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description A highly regiospecific vinylogous carbene insertion protocol for direct asymmetric C–H functionalization of indoles with arylvinyldiazoacetates has been developed. Under the catalysis of simple Rh­(I)/chiral diene complexes, the reaction occurs solely at the vinylogous position of the vinylcarbenoid with exceptional E selectivity and enantiocontrol. It provides an efficient way to obtain an interesting class of chiral indole scaffolds bearing an α,β-unsaturated ester unit and a gem-diaryl carbon stereocenter in good yields (≤99%) with excellent enantioselectivities (≤96%) at room temperature.
doi_str_mv 10.1021/acs.joc.2c02624
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Catalysis
Indoles
Polyenes
Rhodium
Stereoisomerism
title Rhodium(I)-Catalyzed Direct Enantioselective C–H Functionalization of Indoles
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