Preparation of S-(-)-2-Acetoxymethyl-2,5-dihydrofuran and S-(-)-N-Boc-2-hydroxymethyl-2,5-dihydropyrrole by Enzymatic Resolution.

Abstract The enzymatic kinetic resolution of 2-hydroxymethyl-2,5-dihydrofuran and -pyrrole derivatives has been studied. In particular, the acetylation of the primary alcohol as well as the hydrolysis and alcoholysis of the corresponding acetates were investigated in the presence of different lipases. The best results for the multi-gram preparation of S -(−)-2-acetoxymethyl-2,5-dihydrofuran [( S )-(−)- 2 ] with 97% ee were obtained by the alcoholysis of 2 with Candida antarctica . The synthesis of S -(−)- N -Boc-2-hydroxymethyl-2,5-dihydropyrrole [( S )-(−)- 3 ] with up to 98% ee was achieved by its irreversible acetylation catalysed by Pseudomonas fluorescens lipase.