Chiral teleinduction in the polymerization of isocyanides

The effect of the length, constitution and conformation of rod-like spacers between an isocyanide group and a chiral substituent on the diastereoselectivity of the polymerization of these monomers has been studied. The chiral induction has been monitored using circular dichroism spectroscopy as well as polarimetry, and the polymers have also been characterized using NMR, gel permeation chromatography, and MALDI-TOF mass spectrometry. Of the different spacers that have been studied, the benzoate moiety is the most efficient in propagating the chiral information from stereogenic center to the polymer backbone. Remarkably, when this moiety is included in a spacer which separates the stereogenic center from the reactive carbon atom in the monomer by 21 Å an appreciable induction of activity is still observed in the resulting polymer.