posted on 2003-03-18, 00:00authored byGonzalo de Gonzalo, Rosario Brieva, Víctor M. Sánchez, Miguel Bayod, Vicente Gotor
A new chemoenzymatic method for the preparation of an intermediate of (−)-Paroxetine is reported. Cyclic
anhydrides are used as acylating agents in the lipase-catalyzed esterification of trans-4-(4‘-fluorophenyl)-3-hydroxymethyl-N-phenyloxycarbonylpiperidine in organic solvents. The best enantioselectivities are obtained with two
different lipases from Candida antarctica. These two lipases
show opposite stereochemical preference in these processes,
so that both enantiomers can be obtained in their optically
pure forms. The (3S,4R) isomer is an intermediate for the
synthesis of (−)-Paroxetine.