The Bull-James Assembly as a Chiral Auxiliary and Shift Reagent in Kinetic Resolution of Alkyne Amines by the CuAAC Reaction

摘要

The Bull-James boronic acid assembly is used simultaneously as a chiral auxilary 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.