Issue 46, 2016

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

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

Supplementary files

Article information

Article type
Communication
Submitted
29 júl. 2016
Accepted
15 ágú. 2016
First published
06 sep. 2016
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2016,14, 10778-10782

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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