SYNTHESIS OF POLYMERIC CHIRAL OXAZOLINE AND ITS APPLICATIONS ON THE ASYMMETRIC INDUCTION

A series of diastereoisomeric amino bicyclo [2,2,1] heptane derivatives was synthesized from (+)‐camphor. Further treatment of aminobornanols with triethyl orthopropionate afforded chiral oxazolines, which were found to be efficient for the asymmetric induction of carboxylic acids. Synthesis and polymerization of the new chiral oxazolinebornyl methacrylate derived from aminobornanols was carried out. Effects of temperature, solvents, and molar ratio of the reagent on the polymerization of the linear chiral polymers and the synthesis of the insoluble chiral crosslinked polymers were also discussed. Aminobornanols and chiral polymers with pendant aminobornanol moieties were found to be efficient for the asymmetric induction of chiral methylalkanoic acids. Recovery of the chiral reagents, the stereoselectivity of chiral oxazolines, and the parameters governing its successful implementation and the mechanistic aspects of the processes were also investigated. Copyright © 1990 John Wiley & Sons, Inc.