Candida antartica lipase-catalyzed hydrolysis of 4-substituted bis(ethoxycarbonylmethyl) 1,4-dihydropyridine-3,5-dicarboxylates as the key step in the synthesis of optically active dihydropyridines

Prochiral bis(ethoxycarbonylmethyl) substituted 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates were hydrolyzed enantioselectively by Candida antarctica lipase B (Novozym 435). The enantiomeric excesses varied from 68 to 93°depending on the substituent at position 4. In some cases, the e.e. could be s...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: Sobolev, A., Franssen, M.C.R., Makarova, N., Duburs, G., de Groot, Æ.
Format: Article in Journal/Newspaper
Language:English
Published: 2001
Subjects:
Life Science
Antarc*
Antarctica
antartic*
Online Access:https://research.wur.nl/en/publications/candida-antartica-lipase-catalyzed-hydrolysis-of-4-substituted-bi
https://doi.org/10.1016/S0957-4166(00)00441-9
Description
Summary:Prochiral bis(ethoxycarbonylmethyl) substituted 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates were hydrolyzed enantioselectively by Candida antarctica lipase B (Novozym 435). The enantiomeric excesses varied from 68 to 93°depending on the substituent at position 4. In some cases, the e.e. could be significantly increased by changing the solvent system.

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