Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation

William D G Brittain; Andrew G Dalling; Zhenquan Sun; Cécile S Le Duff; Louise Male; Benjamin R Buckley; John S Fossey

doi:10.1038/s41598-019-50940-4

Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation

William D G Brittain, Andrew G Dalling, Zhenquan Sun, Cécile S Le Duff, Louise Male, Benjamin R Buckley, John S Fossey

Chemistry

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3 Citations (Scopus)

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Abstract

A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported. The use of a CuCl (R,R)-Ph-Pybox catalyst system effects a simultaneous kinetic resolution of two racemic starting materials to give one major triazolic diastereoisomer in the ratio 74:12:4:10 (dr 84:16, 90% ee maj). The corresponding control reaction using an achiral copper catalyst gives the four possible diastereoisomers in a 23:27:23:27 ratio, demonstrating minimal inherent substrate control.

Original language	English
Article number	15086
Journal	Scientific Reports
Volume	9
Issue number	1
DOIs	https://doi.org/10.1038/s41598-019-50940-4
Publication status	Published - 21 Oct 2019

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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 = "Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation",

abstract = "A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported. The use of a CuCl (R,R)-Ph-Pybox catalyst system effects a simultaneous kinetic resolution of two racemic starting materials to give one major triazolic diastereoisomer in the ratio 74:12:4:10 (dr 84:16, 90% ee maj). The corresponding control reaction using an achiral copper catalyst gives the four possible diastereoisomers in a 23:27:23:27 ratio, demonstrating minimal inherent substrate control.",

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T1 - Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation

AU - Brittain, William D G

AU - Dalling, Andrew G

AU - Sun, Zhenquan

AU - Duff, Cécile S Le

AU - Male, Louise

AU - Buckley, Benjamin R

AU - Fossey, John S

PY - 2019/10/21

Y1 - 2019/10/21

N2 - A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported. The use of a CuCl (R,R)-Ph-Pybox catalyst system effects a simultaneous kinetic resolution of two racemic starting materials to give one major triazolic diastereoisomer in the ratio 74:12:4:10 (dr 84:16, 90% ee maj). The corresponding control reaction using an achiral copper catalyst gives the four possible diastereoisomers in a 23:27:23:27 ratio, demonstrating minimal inherent substrate control.

AB - A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported. The use of a CuCl (R,R)-Ph-Pybox catalyst system effects a simultaneous kinetic resolution of two racemic starting materials to give one major triazolic diastereoisomer in the ratio 74:12:4:10 (dr 84:16, 90% ee maj). The corresponding control reaction using an achiral copper catalyst gives the four possible diastereoisomers in a 23:27:23:27 ratio, demonstrating minimal inherent substrate control.

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DO - 10.1038/s41598-019-50940-4

M3 - Article

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SN - 2045-2322

VL - 9

JO - Scientific Reports

JF - Scientific Reports

IS - 1

M1 - 15086

ER -

Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation

Abstract

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Boronic Acids for Dye Sensitised Solar Cells

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