The enzyme-mediated preparation of enantiomerically or diastereomerically enriched polycyclic cyanohydrins has been investigated. Oxynitrilase-catalyzed cyanurations gave excellent results with the bicyclic aldehydes tested. On the other hand, enantio- or diastereoselective acylation, catalyzed by lipase PS or subtilisin, proved to be a more versatile methodology, giving good results even with sterically hindered polycyclic cyanohydrins. Specifically, the steroidal cyanohydrin derivative 4b was isolated with a 89% de. (C) 2003 Elsevier Ltd. All rights reserved.
The biocatalyzed stereoselective preparation of polycyclic cyanohydrins
TESSARO, DAVIDE;
2004-01-01
Abstract
The enzyme-mediated preparation of enantiomerically or diastereomerically enriched polycyclic cyanohydrins has been investigated. Oxynitrilase-catalyzed cyanurations gave excellent results with the bicyclic aldehydes tested. On the other hand, enantio- or diastereoselective acylation, catalyzed by lipase PS or subtilisin, proved to be a more versatile methodology, giving good results even with sterically hindered polycyclic cyanohydrins. Specifically, the steroidal cyanohydrin derivative 4b was isolated with a 89% de. (C) 2003 Elsevier Ltd. All rights reserved.File in questo prodotto:
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