Kinetic resolution of a series of benzyl alcohols bearing functional group on α-position catalyzed by (R)-benzotetramisole catalyst has been investigated. The competition between the cation-π interaction of the aryl ring of the substrates with the catalyst and the cation-π interaction of the functional group s π-system with the catalyst led to the decrease of the stereo-selectivity of the reaction and the configuration change of the products.

Key words: kinetic resolution, benzyl alcohols, (R)-benzotetramisole catalyst