CHIRAL GAMMA-HYDROXYSULFONES AND DELTA-HYDROXYSULFONES VIA LIPASE CATALYZED RESOLUTIONS - SYNTHESIS OF (R)(+)-4-HEXANOLIDE AND (2R,5S)-2-METHYL-5-HEXANOLIDE USING INTRAMOLECULAR ACYLATION

Lipase PS-30 (Amano) was found to be an effective catalyst for enantioselective transesterification of a number of racemic gamma and delta hydroxysulfones with isopropenyl acetate in ether. The intramolecular acylation of the ethyl carbonate derivatives obtained from the chiral hydroxysulfones 1d and 1b has been used for the preparation of R(+)-4-hexanolide, sex pheromone of the female dermestid beetle Trogoderma glabrum and (2R, 5S)-2-methyl-5-hexanolide, the sex pheromone of the carpenter bee.