1,3-CYCLOADDITION OF CHIRAL AZOMETHINE YLIDES GENERATED FROM 2-(TERT-BUTYL)-3-METHYLIMIDAZOLIDIN-4-ONE

Authors
PEYRONEL JF GRISONI S CARBONI B COURGEON T CARRIE R
Citation
Jf. Peyronel et al., 1,3-CYCLOADDITION OF CHIRAL AZOMETHINE YLIDES GENERATED FROM 2-(TERT-BUTYL)-3-METHYLIMIDAZOLIDIN-4-ONE, Tetrahedron, 50(1), 1994, pp. 189-198
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
1
Year of publication
1994
Pages
189 - 198
Database
ISI
SICI code
0040-4020(1994)50:1<189:1OCAYG>2.0.ZU;2-6
Abstract
Chiral azomethine ylides, easily generated from 2-(tert-butyl)-3-methy l-imidazolidin-4-one and aldehydes, undergo 1,3-dipolar cycloadditions to activated alkenes. These reactions proceed with complete facial st ereoselection. In the case of benzaldehyde and hexanal, the configurat ions of the 1,3-dipoles are also controlled and these ylides display h igh diastereoselectivity in their reactions with N-phenylmaleimide.