Enzymatic kinetic resolution of (±)-4-acetoxy[2.2]paracyclophane by Candida cylindracea lipase. An efficient route for the preparation of (+)-R-4-hydroxy- and (+)-S-4-acetoxy[2.2]paracyclophane

Abstract

The enzymatic kinetic resolution of (±)-4-acetoxy[2.2]paracyclophane by Candida cylindracea lipase was investigated in water and in a two-phase aqueous organic system. The (+)-(R)-4-hydroxy- and (+)-(S)-4-acetoxy[2.2]-paracyclophanes were isolated in excellent yields and high enantiomeric excesses. The resolution was carried out on multi-gram scale in hexane-water at 40° C.