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

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...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-02, Vol.10 (3), p.473-486
Main Authors: Quirós, Margarita, Rebolledo, Francisca, Gotor, Vicente
Format: Article
Language:English
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Summary: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.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00016-6