Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

Abstract

We herein report a method for the kinetic resolution of racemic 4-hydroxy[2.2]paracyclophane by means of a chiral isothiourea-catalyzed acylation with isobutyric anhydride. This protocol allows for a reasonable synthetically useful s-factor of 20 and provides a novel entry to obtain this interesting planar chiral motive in an enantioenriched manner.

Keywords

• acylation
• kinetic resolution
• nucleophilic catalysis
• paracyclophanes
• planar chirality