Enzymatic resolution of a quaternary stereogenic centre as the key step in the synthesis of (S)-(+)-citalopram |
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| Affiliation: | 1. Facultad de Quı́mica, Departamento de Quı́mica Orgánica e Inorgánica, Universidad de Oviedo, 33071 Oviedo, Spain;2. Astur-Pharma S.A. Polı́gono Industrial de Silvota, parcela 23, 33192 Llanera (Asturias), Spain;1. Department of Building Materials Technology, Faculty of Materials Science and Ceramics, AGH University of Science and Technology, Mickiewicza 30, 30-059 Krakow, Poland;2. Non affiliated;1. School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK;2. Department of Metallurgy and Materials, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece;2. Department of Animal & Human Physiology, Faculty of Biology, University of Athens, Panepistimiopolis, Athens 15784, Greece |
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| Abstract: | The enzymatic resolution of 4-[(4-dimethylamino)-1-(4′-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)-benzonitrile, a useful intermediate in the synthesis of enantiomerically pure citalopram, has been studied. Candida antarctica lipase B (CAL-B) catalyzes the enzymatic acetylation of the primary benzylic alcohol with high enantioselectivity at the quaternary stereogenic centre. The enzymatic enantioselective hydrolysis of the 3-acetyloxymethyl derivative catalyzed by CAL-B is also possible. |
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