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.
Highlights
A non-enzymatic simultaneous kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported
Catalytic kinetic resolution (KR) occurs when one enantiomer of a racemic substrate is preferentially activated towards reaction by a chiral catalyst, leading to more rapid formation of one enantiomer of product
Catalytic KR has been successfully employed in copper-catalysed azide-alkyne cycloadditions leading to enantioenriched chiral triazoles and the recovery of enantioenriched starting materials (Scheme 1i and ii)[17,18,19,20,21], and complete consumption of starting materials in the case of dynamic kinetic resolution[22]
Summary
A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, utilising an asymmetric CuAAC reaction is reported. Catalytic KR has been successfully employed in copper-catalysed azide-alkyne cycloadditions leading to enantioenriched chiral triazoles and the recovery of enantioenriched starting materials (Scheme 1i and ii)[17,18,19,20,21], and complete consumption of starting materials in the case of dynamic kinetic resolution[22]. Upon coetaneous resolution of two racemic substrates, the ideal scenario would be formation, at 50% conversion, of a single diastereoisomer of the product formed from one enantiomer of each substrate. This ideal process would leave the opposite
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