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.

SUBMITTER: Brittain WDG 

PROVIDER: S-EPMC6803658 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature