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

Research output: Contribution to journalArticle

Authors

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

Colleges, School and Institutes

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.

Details

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