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

William D. G. Brittain; Brette M. Chapin; Wenlei Zhai; Vincent M. Lynch; Benjamin R. Buckley; Eric V. Anslyn; John S. Fossey

doi:10.1039/C6OB01623E

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

William D. G. Brittain, Brette M. Chapin, Wenlei Zhai, Vincent M. Lynch, Benjamin R. Buckley, Eric V. Anslyn, John S. Fossey

Chemistry

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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.

Original language	English
Journal	Organic and Biomolecular Chemistry
Early online date	6 Sept 2016
DOIs	https://doi.org/10.1039/C6OB01623E
Publication status	E-pub ahead of print - 6 Sept 2016

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10.1039/C6OB01623ELicence: Creative Commons: Attribution (CC BY)

Brittain_et_al_Bull-James_Assembly_Organic_Biomolecular_ChemistryFinal published version, 386 KBLicence: Creative Commons: Attribution (CC BY)

Boronic Acids for Dye Sensitised Solar Cells
Fossey, J.
Engineering & Physical Science Research Council
23/04/12 → 22/04/14
Project: Research

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title = "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.",

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AU - Brittain, William D. G.

AU - Chapin, Brette M.

AU - Zhai, Wenlei

AU - Lynch, Vincent M.

AU - Buckley, Benjamin R.

AU - Anslyn, Eric V.

AU - Fossey, John S.

PY - 2016/9/6

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N2 - 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.

AB - 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.

U2 - 10.1039/C6OB01623E

DO - 10.1039/C6OB01623E

M3 - Article

SN - 1477-0520

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

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

Abstract

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Boronic Acids for Dye Sensitised Solar Cells

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