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Issue 4, 2014
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Catalytic enantioselective synthesis of 2-(2-hydroxyethyl)indole scaffolds via consecutive intramolecular amido-cupration of allenes and asymmetric addition of carbonyl compounds

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Abstract

A catalytic enantioselective method for the synthesis of 2-(2-hydroxyethyl)indole scaffolds was developed. The process includes catalytic intramolecular amido-cupration of an allene to generate a novel allylcopper species, followed by asymmetric addition of the thus-generated chiral nucleophile to aldehydes and ketones. This is the first example of catalytic indole formation coupled with asymmetric C–C bond formation via in situ generation of a reactive chiral allylcopper species.

Graphical abstract: Catalytic enantioselective synthesis of 2-(2-hydroxyethyl)indole scaffolds via consecutive intramolecular amido-cupration of allenes and asymmetric addition of carbonyl compounds

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Publication details

The article was received on 08 Oct 2013, accepted on 20 Dec 2013 and first published on 23 Dec 2013


Article type: Edge Article
DOI: 10.1039/C3SC52803K
Chem. Sci., 2014,5, 1585-1590

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    Catalytic enantioselective synthesis of 2-(2-hydroxyethyl)indole scaffolds via consecutive intramolecular amido-cupration of allenes and asymmetric addition of carbonyl compounds

    P. K. Chikkade, Y. Shimizu and M. Kanai, Chem. Sci., 2014, 5, 1585
    DOI: 10.1039/C3SC52803K

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