Formation of a cyclopropane ester on a polymer support: effect of the macromolecular backbone on the stereoselectivity of cyclization

Abstract

The stereoselectivity of cyclopropane ester formation was studied using reagents supported on linear or crosslinked polymers, and was compared with that obtained from low-molecular-weight compounds. The most important effects were noted with the crosslinked resin (2% DVB), in binary solvents or by lowering the temperature. The solvent effect was attributed to a specific solvation of the resin by one component of the mixture. The temperature influence would be the result of a restricted mobility of the macromolecular chain.