T. Steinhausler et F. Stelzer, OPTICALLY-ACTIVE POLYMERS VIA RING-OPENING METATHESIS POLYMERIZATION .2. POLYMERIZATION OF ENANTIOMERICALLY PURE (-)-ENDO-2-NORBORNENYL ACETATE, Journal of molecular catalysis, 90(1-2), 1994, pp. 53-60
(-)-endo-2-Acetoxy-bicyclo [2.2.1]hept-5-ene ((-)-endo-2-norbornenyl a
cetate) was synthesized from (-)-endo-2-norbornenyl butyrate which was
separated from the racemic mixture by enzymatic hydrolysis using Cand
ida cylindracea lipase to provide monomers with high enantiomeric puri
ty (ee > 95%). The monomer was polymerized via ring opening metathesis
polymerization (ROMP) using Mo(CH-t-Bu) (NAr) (0-t-Bu) 2 and other si
milar molybdenum-carbene catalysts in different solvents. All reaction
s yielded optically active polymers with the specific rotation [alpha]
D depending on catalyst and solvent. Spectroscopic data (IR, NMR) of t
he polymers show the influences of catalysts and solvents on the stere
ochemistry of the polymerization reaction.