Candida antarctica 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

Authors
Sobolev, A Franssen, MCR Makarova, N Duburs, G de Groot, A
Citation
A. Sobolev et al., Candida antarctica 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, TETRAHEDR-A, 11(22), 2000, pp. 4559-4569
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
22
Year of publication
2000
Pages
4559 - 4569
Database
ISI
SICI code
0957-4166(20001117)11:22<4559:CALHO4>2.0.ZU;2-1
Abstract
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%, d epending on the substituent at position 4. In some cases, the e.e. could be significantly increased by changing the solvent system. (C) 2000 Elsevier Science Ltd. All rights reserved.