Asymmetric synthesis of bicyclic diol derivatives through metal and enzyme catalysis: Application to the formal synthesis of sertraline
2010 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 13, 4031-4036 p.Article in journal (Refereed) Published
Enzyme- and ruthenium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) of bicyclic diols to their diacetates was highly enantio- and diastereoselective to give the corresponding diacetates in high yield with high enantioselectivity (99.9 % ee). The enantiomerically pure diols are accessible by simple hydrolysis (NaOH, MeOH), but an alternative enzyme-catalyzed ester cleavage was also used to give the trans-diol (R,R)-1 b in extremely high diastereomeric purity (trans/cis=99.9:0.1, >99.9 % ee). It was demonstrated that the diols can be selectively oxidized to the ketoalcohols in a ruthenium-catalyzed Oppenauer-type reaction. A formal enantioselective synthesis of sertraline from a simple racemic cis/trans diol 1 b was demonstrated.
Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA , 2010. Vol. 16, no 13, 4031-4036 p.
IdentifiersURN: urn:nbn:se:su:diva-47342DOI: 10.1002/chem.200903114ISI: 000276735900020OAI: oai:DiVA.org:su-47342DiVA: diva2:373699
FunderSwedish Research Council
authorCount :32010-12-012010-12-012011-02-25Bibliographically approved