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Issue 46, 2016
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The Bull–James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction

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Abstract

The Bull–James boronic acid assembly is used simultaneously as a chiral auxiliary for kinetic resolution and as a chiral shift reagent for in situ enantiomeric excess (ee) determination by 1H NMR spectroscopy. Chiral terminal alkyne-containing amines, and their corresponding chiral triazoles formed via CuAAC, were probed in situ. Selectivity factors of up to s = 4 were imparted and measured, accurate to within ±3% when compared to chiral GC.

Graphical abstract: The Bull–James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction

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Supplementary files

Article information


Submitted
29 Jul 2016
Accepted
15 Aug 2016
First published
06 Sep 2016

This article is Open Access

Org. Biomol. Chem., 2016,14, 10778-10782
Article type
Communication

The Bull–James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction

W. D. G. Brittain, B. M. Chapin, W. Zhai, V. M. Lynch, B. R. Buckley, E. V. Anslyn and J. S. Fossey, Org. Biomol. Chem., 2016, 14, 10778
DOI: 10.1039/C6OB01623E

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