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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 meso -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 ( S )-GABOB.

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