Diastereocontrolled reduction of cyclic beta-enaminones. A new diastereoselective route to 2,6-disubstituted piperidines

Authors
Freville, S Delbecq, P Thuy, VM Petit, H Celerier, JP Lhommet, G
Citation
S. Freville et al., Diastereocontrolled reduction of cyclic beta-enaminones. A new diastereoselective route to 2,6-disubstituted piperidines, TETRAHEDR L, 42(28), 2001, pp. 4609-4611
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
28
Year of publication
2001
Pages
4609 - 4611
Database
ISI
SICI code
0040-4039(20010709)42:28<4609:DROCBA>2.0.ZU;2-A
Abstract
A new diastereoselective synthesis of 2,6-disubstituted piperidinic alkaloi ds is presented. Three natural compounds, the (-)-pinidinone 1a, the (+)-di hydiopinidine 1b and the (-)-pinidinol 1c were prepared from optically pure (6R)-6-methylpiperidin-2-one 2. This method is based on thc chemo- and dia stereocontrolled reductions of an exocyclic beta -enamino ketone. (C) 2001 Elsevier Science Ltd. All rights reserved.