engleski

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

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 (84-97% de). Optically pure alcohols were prepared using lipase-catalyzed kinetic resolution of 2-ethylhexanol using vinyl laurate as acyl donor.

kinetic resolution ; meso-anhydrides ; desymmetrization ; fragrances

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