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Diastereo- and enantioselective phase-transfer alkylation of 3-substituted oxindoles with racemic secondary alkyl halides

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Abstract

A catalytic asymmetric alkylation of fully substituted enolates with racemic, non-activated secondary alkyl halides is described. The chiral 1,2,3-triazolium ion enables excellent diastereo- and enantiocontrol via enantiofacial discrimination of prochiral enolates and kinetic resolution of secondary halides.

Graphical abstract: Diastereo- and enantioselective phase-transfer alkylation of 3-substituted oxindoles with racemic secondary alkyl halides

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The article was received on 12 Sep 2017, accepted on 26 Oct 2017 and first published on 26 Oct 2017


Article type: Communication
DOI: 10.1039/C7CC07122A
Citation: Chem. Commun., 2017, Advance Article
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    Diastereo- and enantioselective phase-transfer alkylation of 3-substituted oxindoles with racemic secondary alkyl halides

    K. Ohmatsu, Y. Furukawa, M. Kiyokawa and T. Ooi, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC07122A

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