STEREOSELECTIVE SYNTHESIS OF FLUORINATED MATERIALS CATALYZED BY AN ANTIBODY

A monoclonal antibody, elicited by a transition-state analogue for the hydrolysis of fluorinated esters, acted as an enzymelike catalyst for the preparation of chiral fluorinated compounds. The syntheses of (R)- or (S)-1-(fluoroalkyl)alkanols and an allylic alcohol possessing a trifluoromethyl group in high optical purity (> 98% enantiomeric excess (ee)) by antibody-derived reagents are described. The role of molecular recognition by antibody reagents and its importance to the preparation of optically pure materials is described. Significantly, it has been found that a fluoromethyl group on the stereogenic center or an acyloyl group enhanced the optical purity of the resultant products.