ENANTIOSELECTIVE PROTONATION OF AMIDE ENOLATES DERIVED FROM PIPERIDINE-2-CARBOXYLIC ACID

Authors
MARTIN J LASNE MC PLAQUEVENT JC DUHAMEL L
Citation
J. Martin et al., ENANTIOSELECTIVE PROTONATION OF AMIDE ENOLATES DERIVED FROM PIPERIDINE-2-CARBOXYLIC ACID, Tetrahedron letters, 38(41), 1997, pp. 7181-7182
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
41
Year of publication
1997
Pages
7181 - 7182
Database
ISI
SICI code
0040-4039(1997)38:41<7181:EPOAED>2.0.ZU;2-0
Abstract
Enantioselective protonation was applied on amide enolates 1a and 2a, derived from piperidine-2-carboxylic acid. High enantioselectivity was obtained with diamine (+)-3, as chiral source, and in presence of LiB r. Up to 95+/-1% ee for amide 1 and >99% for amide 2 were reached. Mor eover, (S)-1 and (R)-1 were obtained with 89% and 93% ee using (+) and (-) ephedrine respectively. (C) 1997 Elsevier Science Ltd.