Novel asymmetric dealkoxycarbonylation of 3-oxo-8-azabicyclo[3.2.1]- octane-2,4-dicarboxylates using porcine liver esterase: A new route to (-)- anhydroecgonine methyl ester

Article abstract of DOI:10.1016/S0040-4039(99)00976-4

The porcine liver esterase-catalyzed dealkoxycarbonylation of 8-benzyl- 3-oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylates (4) was found to give high enantiomeric excess of the desymmetrized keto ester (5). This novel dealkoxylcarbonylation opened a new route to the asymmetric synthesis of (1R)-cocaine related radiopharmaceuticals such as (1R)-β-CIT, for diagnosis of Parkinson's disease.