Issue 98, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
12 Sep 2017
Accepted
26 Oct 2017
First published
26 Oct 2017

Chem. Commun., 2017,53, 13113-13116

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, 53, 13113 DOI: 10.1039/C7CC07122A

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