Enzymatic resolution of a quaternary stereogenic centre as the key step in the synthesis of ( S)-(+)-citalopram

Graphic 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 th...

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Published in:Tetrahedron: asymmetry 2004-01, Vol.15 (2), p.341-345
Main Authors: Solares, Laura F., Brieva, Rosario, Quirós, Margarita, Llorente, Isidro, Bayod, Miguel, Gotor, Vicente
Format: Article
Language:English
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Summary:Graphic 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.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2003.10.022