Pig liver esterase (PLE)-mediated resolution of N-substituted 4-benzoyloxy-3-carbomethoxypiperidines: a convenient preparation of 4-hydroxy- and 4-benzoyloxy-3-carbomethoxypiperidines in enantiomerically pure form

Authors
Roberti, M Rondanin, R Ferroni, R Baruchello, R Invidiata, FP Andrisano, V Bertucci, C Bertolasi, V Grimaudo, S Tolomeo, M Simoni, D
Citation
M. Roberti et al., Pig liver esterase (PLE)-mediated resolution of N-substituted 4-benzoyloxy-3-carbomethoxypiperidines: a convenient preparation of 4-hydroxy- and 4-benzoyloxy-3-carbomethoxypiperidines in enantiomerically pure form, TETRAHEDR-A, 11(21), 2000, pp. 4397-4405
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
21
Year of publication
2000
Pages
4397 - 4405
Database
ISI
SICI code
0957-4166(20001103)11:21<4397:PLE(RO>2.0.ZU;2-Z
Abstract
Pig liver esterase (PLE) afforded smooth chemical resolution of racemic N-s ubstituted 4-(benzoyloxy)3-carbomethoxypiperidines. The enzyme showed good chemo- and enantioselective properties, thus allowing discrimination betwee n the carbomethoxy and benzoate ester groups, the latter being more easily hydrolyzed. The proposed methodology also represents a practical means for the procurement of N-substituted 4-hydroxy-3-carbomethoxypiperidines in ena ntiomerically pure form. (C) 2000 Elsevier Science Ltd. All rights reserved .