The biocatalyzed stereoselective preparation of polycyclic cyanohydrins

• Author(s): Silva, M. Manuel Cruz ; Melo, M. Luísa Sá e ; Parolin, Marco ; Tessaro, Davide ; Riva, Sergio ; Danieli, Bruno
• Date: 2004
• Persistent ID: http://hdl.handle.net/10316/5771
• Origin: Estudo Geral - Universidade de Coimbra
• Document Type: Article
• Language: English

Description

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. http://www.sciencedirect.com/science/article/B6THT-4B53Y32-2/1/840d22acaac2079965efb41cc790103e