Enzymatic desymmetrization of meso cis-2,6-and cis,cis-2,4,6-substituted piperidines. Chemoenzymatic synthesis of (5S,9S)-(+)-indolizidine 209D

Authors
Chenevert, R Ziarani, GM Morin, MP Dasser, M
Citation
R. Chenevert et al., Enzymatic desymmetrization of meso cis-2,6-and cis,cis-2,4,6-substituted piperidines. Chemoenzymatic synthesis of (5S,9S)-(+)-indolizidine 209D, TETRAHEDR-A, 10(16), 1999, pp. 3117-3122
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
16
Year of publication
1999
Pages
3117 - 3122
Database
ISI
SICI code
0957-4166(19990813)10:16<3117:EDOMCC>2.0.ZU;2-C
Abstract
The stereoselective acylation of meso piperidines 3a,b by vinyl acetate (so lvent and acyl donor) in the presence of Candida antarctica lipase gave the corresponding (2S,6R) and (2S,4R,6R) monoesters 2a,b in high enantiomeric purity. (5S,9S)-(+)-Indolizidine 209D was prepared in eight steps from (2S, 6R)-2a. (C) 1999 Elsevier Science Ltd. All rights reserved.