Synthesis and metathesis polymerization of (1r,2r,6s,7s)-4-(1-phenylethyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Herein, we report the synthesis of a racemic monomer (1r,2r,6s,7s)-4-(1-phenylethyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione and its metathesis polymerization. The desired monomer was successfully prepared from exo-5-norbornene-2,3-dicarboxyanhydride (exo-NDA) and 1-phenylethylamine. The obtained monomer exhibited a good reactivity in ROMP polymerization over the 1st generation Grubbs catalyst. High molecular weight, soluble and amorphous polymer was isolated in a high yield. The realized approach opens an efficient way towards the synthesis of various optically active polymers based on exo-NDA and chiral amines.