PREPARATION OF S-(-)-2-ACETOXYMETHYL-2,5-DIHYDROFURAN AND S-(-)-N-BOC-2-HYDROXYMETHYL-2,5-DIHYDROPYRROLE BY ENZYMATIC RESOLUTION

The enzymatic kinetic resolution of 2-hydroxymethyl-2,5-dihydrofuran a nd -pyrrole derivatives has been studied. In particular, the acetylati on of the primary alcohol as well as the hydrolysis and alcoholysis of the corresponding acetates were investigated in the presence of diffe rent lipases. The best results for the multi-gram preparation of S-(-) -2-acetoxymethyl-2,5-dihydrofuran [(S)-(-)-2] with 97% ee were obtaine d 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 Pseudom onas fluorescens lipase. (C) 1998 Elsevier Science Ltd. All rights res erved.