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

Research output: Contribution to journal › Article › peer-review

Standard

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.

Research output: Contribution to journal › Article › peer-review

Harvard

Brittain, WDG, Dalling, AG, Sun, Z, Duff, CSL, Male, L, Buckley, BR & Fossey, JS 2019, 'Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation', Scientific Reports, vol. 9, no. 1, 15086. https://doi.org/10.1038/s41598-019-50940-4

APA

Brittain, W. D. G., Dalling, A. G., Sun, Z., Duff, C. S. L., Male, L., Buckley, B. R., & Fossey, J. S. (2019). Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation. Scientific Reports, 9(1), [15086]. https://doi.org/10.1038/s41598-019-50940-4

Vancouver

Brittain WDG, Dalling AG, Sun Z, Duff CSL, Male L, Buckley BR et al. Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation. Scientific Reports. 2019 Oct 21;9(1). 15086. https://doi.org/10.1038/s41598-019-50940-4

Author

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 -