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

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 H NMR spectroscopy. Chiral terminal alkyne-containing amines, and their corresponding chiral triazoles formed v...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-11, Vol.14 (46), p.10778-10782
Main Authors: Brittain, William D G, Chapin, Brette M, Zhai, Wenlei, Lynch, Vincent M, Buckley, Benjamin R, Anslyn, Eric V, Fossey, John S
Format: Article
Language:English
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Summary: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 H 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01623e