Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of -cyclic anhydrides.

A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of -cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of ()-GABOB.