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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Colleges, School and Institutes
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.
|Journal||Organic and Biomolecular Chemistry|
|Early online date||6 Sep 2016|
|Publication status||E-pub ahead of print - 6 Sep 2016|