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Resolution of the diols of bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane and bicyclo[3.2.1]octane by enzymic hydrolysis, and their absolute configurations

1992; Issue: 18 Linguagem: Inglês

10.1039/p19920002337

2050-8255

Kōichirō Naemura, Nobuo Takahashi, Shunsuke Tanaka, Hirotsugu Ida,

Microbial Metabolic Engineering and Bioproduction

Enzyme (pig liver esterase and lipase from Aspergillus niger)-catalysed enantioselective hydrolyses of racemic diacetates, (1R*,2S*,4R*,5S*)- and (1R*,2R*,4R*,5R*)-2,5-diacetoxybicyclo[2.2.1]heptanes, (1R*,2S*,4R*,5S*)-, (1R*,2R*,4R*,5R*)- and (1R*,2R*,4R*,5S*)-2,5-diacetoxybicyclo[2.2.2]-octanes, (2R*,3R*)-2,3-diacetoxybicyclo[2.2.2]octane and (1R*,2S*,6S*,8R*)- and (1R*,2S*,6S*,8S*)-2,8-diacetoxybicyclo[3.2.1]octanes gave the corresponding monoacetates and the recovered diacetates in an optically active form. The absolute configurations of products were unequivocally determined by chemical correlation to the corresponding known monoacetates, (2S)-(+)-2-acetoxybicyclo[2.2.1]heptane, (2S)-(+)-2-acetoxybicyclo[2.2.2]octane and (2S)-(+)-2-acetoxybicyclo[3.2.1 ]octane, and circular dichroism spectra of keto acetates and diketones derived from the hydrolysis products were examined.