Lipase catalyzed asymmetrization of quinolyl substituted 1,3-propanediols

2-(2-Quinolyl)- and 2-(4-quinolyl)-1,3-propanediols 3 and 4 were prepared and asymmetrized by enantioselective acetylation in organic solvent catalyzed by lipases. While monoacetate 5 was best obtained using Celite-supported pig pancreatic lipase (PPL) (97.3% e.e.) as the ( R)-enantiomer, both enant...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 9; no. 14; pp. 2481 - 2492
Main Authors Banfi, Luca, Guanti, Giuseppe, Mugnoli, Angelo, Riva, Renata
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.07.1998
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
DIOLS
DYNEMICIN-A
REAGENTS
LIGANDS
ENANTIOMERS
RESOLUTION
CHEMISTRY
MONOACETYLATION
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Summary:2-(2-Quinolyl)- and 2-(4-quinolyl)-1,3-propanediols 3 and 4 were prepared and asymmetrized by enantioselective acetylation in organic solvent catalyzed by lipases. While monoacetate 5 was best obtained using Celite-supported pig pancreatic lipase (PPL) (97.3% e.e.) as the ( R)-enantiomer, both enantiomers of 6 have been obtained using different enzymes: ( R)- 6 using lipase from Aspergillus niger (84.0% e.e.) and ( S)- 6 using lipase from Candida antarctica (97.5% e.e.). The absolute configuration of both monoacetates 5 and 6 has been determined by anomalous X-ray dispersion methodology on the corresponding p-bromobenzoates 11 and 12.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(98)00247-X