ENANTIOSELECTIVE ACCESS TO 5-MEMBERED AND 6-MEMBERED NITROGEN-CONTAINING HETEROCYCLES, BASED ON THE ASYMMETRIC MICHAEL ADDITION OF CHIRAL IMINES AND CHIRAL ENAMINO ESTERS

Authors
DANGELO J CAVE C DESMAELE D GASSAMA A THOMINIAUX C RICHE C
Citation
J. Dangelo et al., ENANTIOSELECTIVE ACCESS TO 5-MEMBERED AND 6-MEMBERED NITROGEN-CONTAINING HETEROCYCLES, BASED ON THE ASYMMETRIC MICHAEL ADDITION OF CHIRAL IMINES AND CHIRAL ENAMINO ESTERS, Heterocycles, 47(2), 1998, pp. 725-746
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
47
Issue
2
Year of publication
1998
Pages
725 - 746
Database
ISI
SICI code
0385-5414(1998)47:2<725:EAT5A6>2.0.ZU;2-D
Abstract
The addition reaction of chiral imines, (ent-10, 48, 70) and chiral en amino esters (52, 55, 73) with maleic anhydride (32), citraconic anhyd ride (57), alpha-chloroacrylonitrile (29), and nitroethylene (74), has been investigated. These condensations proved to be in general highly regio-, diastereo-, and enantioselective. In most cases the primary a dducts underwent an in situ N-heterocyclization, allowing the enantios elective access to nitrogen-containing, five- and six-membered heteroc ycles.