A CONCISE PROCEDURE FOR THE PREPARATION OF ENANTIOPURE 3-ALKYLPIPERIDINES

Authors
AMAT M LLOR N HIDALGO J BOSCH J
Citation
M. Amat et al., A CONCISE PROCEDURE FOR THE PREPARATION OF ENANTIOPURE 3-ALKYLPIPERIDINES, Tetrahedron : asymmetry, 8(13), 1997, pp. 2237-2240
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
13
Year of publication
1997
Pages
2237 - 2240
Database
ISI
SICI code
0957-4166(1997)8:13<2237:ACPFTP>2.0.ZU;2-S
Abstract
Reaction of (R)-phenylglycinol with racemic methyl 4-formylhexanoate t akes place with a remarkable stereoselectivity to give two diastereome ric 6-ethyloxazolopiperidones (9:1 ratio) in 76% overall yield. After LiAlH4 reduction and catalytic hydrogenation, the major isomer was con verted to (S)-3-ethylpiperidine. (C) 1997 Elsevier Science Ltd.