Issue 97, 2015
From the journal:

Chemical Communications

Kinetic resolution of alkyne-substituted quaternary oxindoles via copper catalysed azide–alkyne cycloadditions†

William D. G. Brittain,a   Benjamin R. Buckley‡*b  and  John S. Fossey‡*a  

* Corresponding authors

a School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands, UK
E-mail: j.s.fossey@bham.ac.uk

b Department of Chemistry, Loughborough University, Loughborough, Leicestershire, UK
E-mail: b.r.buckley@lboro.ac.uk

Abstract

The synthesis and kinetic resolution of quaternary oxindoles through copper catalysed azide–alkyne cycloadditions is presented. Selectivity factors (s) up to 22.1 ± 0.5 are reported. Enantioenriched alkynes and triazoles were obtained in ≥80% enantiomeric excess (e.e.).

Graphical abstract: Kinetic resolution of alkyne-substituted quaternary oxindoles via copper catalysed azide–alkyne cycloadditions

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Article information

DOI
https://doi.org/10.1039/C5CC04886A
Article type
Communication
Submitted
12 Jun 2015
Accepted
12 Aug 2015
First published
27 Aug 2015
This article is Open Access
Creative Commons BY license

Chem. Commun., 2015,51, 17217-17220

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Kinetic resolution of alkyne-substituted quaternary oxindoles via copper catalysed azide–alkyne cycloadditions

W. D. G. Brittain, B. R. Buckley and J. S. Fossey, Chem. Commun., 2015, 51, 17217 DOI: 10.1039/C5CC04886A

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