A PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF EPIBATIDINE

Authors
SZANTAY C KARDOSBALOGH Z MOLDVAI I SZANTAY C TEMESVARIMAJOR E BLASKO G
Citation
C. Szantay et al., A PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF EPIBATIDINE, Tetrahedron, 52(33), 1996, pp. 11053-11062
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
33
Year of publication
1996
Pages
11053 - 11062
Database
ISI
SICI code
0040-4020(1996)52:33<11053:APESOE>2.0.ZU;2-4
Abstract
Two different syntheses of Epibatidine (1) were designed and carried o ut using easily accessible reagents and convenient reaction conditions . The ring closure of the prochiral precursor 4 catalyzed by optically active alpha-phenyl-ethyl-amine gave the key intermediate 5 in over 8 0% ee from which the natural product (-)-1 has been prepared. Copyrigh t (C) 1996 Elsevier Science Ltd