Desymmetrization of cyclic anhydrides mediated by cinchona alkaloids: synthesis and olfactory properties of new fragrances based on (R)- and (S)-2-ethylhexanol

Abstract

A series of enantiomerically pure new fragrances, derived from 2-ethylhexanol, have been prepared and their olfactory properties evaluated. The key step of the synthesis is cinchona-alkaloid-catalyzed desymmetrization of cyclic meso-anhydrides with (R)- and (S)-2-ethylhexanol and proceeded in good to excellent diastereoselectivities (92:8-98:2 dr). Enantiomerically pure alcohols were prepared by lipase-catalyzed kinetic resolution of 2-ethylhexanol using vinyl laurate as acyl donor.