GUANIDINIUM CATALYZED CONJUGATE ADDITION OF PYRROLIDINE TO UNSATURATED LACTONES

Authors
ALCAZAR V MORAN JR DEMENDOZA J
Citation
V. Alcazar et al., GUANIDINIUM CATALYZED CONJUGATE ADDITION OF PYRROLIDINE TO UNSATURATED LACTONES, Tetrahedron letters, 36(22), 1995, pp. 3941-3944
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
22
Year of publication
1995
Pages
3941 - 3944
Database
ISI
SICI code
0040-4039(1995)36:22<3941:GCCAOP>2.0.ZU;2-Q
Abstract
More than a 8-fold reduction in half-life can be observed for conjugat e additions of pyrrolidine to alpha,beta-unsaturated lactones in the p resence of catalytic amounts (0.1 equiv.) of bicyclic chiral guanidini um salts 1, presumably by selective hydrogen-bond stabilization of the transition state.