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

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
84 Downloads (Pure)

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 languageEnglish
Article number15086
JournalScientific Reports
Volume9
Issue number1
DOIs
Publication statusPublished - 21 Oct 2019

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