Bioreduction of 2-oxocyclopentanecarboxamides: Syntheses of optically active 2-aminomethyl- and 2-aminocyclopentanols

Abstract

The fungus Mortierella isabellina NRRL 1757 catalyzes the reduction of 2-oxocyclopentanecarboxamides with very high enantioselectivity giving; in most cases, the corresponding enantiopure 2-hydroxycyclopentanecarboxamides. The presence or absence of a substituent on the amidic nitrogen has a strong influence on the diastereoselectivity achieved in these processes. Optically active hydroxyamides prepared in these microbial reductions are used as starting materials for the preparation of optically active 2-aminomethyl- and 2-aminocyclopentanols.