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

Citation data:

Organic & biomolecular chemistry, ISSN: 1477-0539, Vol: 14, Issue: 46, Page: 10778-10782

Publication Year:
2016
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PMID:
27604036
DOI:
10.1039/c6ob01623e
PMCID:
PMC5121074
Author(s):
Brittain, William D G; Chapin, Brette M; Zhai, Wenlei; Lynch, Vincent M; Buckley, Benjamin R; Anslyn, Eric V; Fossey, John S
Publisher(s):
Royal Society of Chemistry (RSC); The Royal Society of Chemistry
Tags:
Biochemistry, Genetics and Molecular Biology; Chemistry
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article description
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.