Abstract
An improved procedure for the kinetic resolution of endo- endo- cis-bicyclo[3.3.0]octane-2,6-diol rac- 1 ) by transesterification with vinyl acetate catalysed by lipase from Pseudomonas cepacia in an organic solvent which yields both enantiomers with an enantiomeric excess of >95% is described. The configuration at both stereogenic centres bearing hydroxy groups has been inverted by treatment of the corresponding mesylates with caesium acetate in the presence of 18-crown-6 to afford, after deacetylation, the corresponding enantiomerically pure diastereoisomeric exo- exo- cis-diols.
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