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

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Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation. / Brittain, William D G; Dalling, Andrew G; Sun, Zhenquan; Duff, Cécile S Le; Male, Louise; Buckley, Benjamin R; Fossey, John S.

In: Scientific Reports, Vol. 9, No. 1, 15086, 21.10.2019.

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Brittain, William D G ; Dalling, Andrew G ; Sun, Zhenquan ; Duff, Cécile S Le ; Male, Louise ; Buckley, Benjamin R ; Fossey, John S. / Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation. In: Scientific Reports. 2019 ; Vol. 9, No. 1.

Bibtex

@article{71e322d3e0b94f52843e67c553120882,
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.",
author = "Brittain, {William D G} and Dalling, {Andrew G} and Zhenquan Sun and Duff, {C{\'e}cile S Le} and Louise Male and Buckley, {Benjamin R} and Fossey, {John S}",
year = "2019",
month = oct,
day = "21",
doi = "10.1038/s41598-019-50940-4",
language = "English",
volume = "9",
journal = "Scientific Reports",
issn = "2045-2322",
publisher = "Nature Publishing Group",
number = "1",

}

RIS

TY - JOUR

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.

U2 - 10.1038/s41598-019-50940-4

DO - 10.1038/s41598-019-50940-4

M3 - Article

C2 - 31636274

VL - 9

JO - Scientific Reports

JF - Scientific Reports

SN - 2045-2322

IS - 1

M1 - 15086

ER -