Journal article

Enzymatic resolution of tropinone derivatives

The lipase-mediated kinetic resoln. of racemic scopoline and 6-hydroxytropinone is reported. Whereas (±)-scopoline is difficult to resolve due to steric hindrance of the hydroxy function, the resoln. of (±)-6-hydroxytropinone with vinyl acetate as acyl donor gave alc. (+)-6-hydroxytropinone and the corresponding acetate (-)-6-acetoxytropinone with high enantiomeric excess. In case of the optimal result of 99% ee for (+)-6-hydroxytropinone and 80% ee for (-)-6-acetoxytropinone, an E-value of 35 was calcd. The preparative lipase-catalyzed resoln. of (±)-6-hydroxytropinone resulted in almost enantiopure alc. (+)-6-hydroxytropinone with >99% ee after one recrystn.


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