RING-OPENING CYCLOADDITION OF AZIRIDINES TO KETENIMINES

Authors
MAAS H BENSIMON C ALPER H
Citation
H. Maas et al., RING-OPENING CYCLOADDITION OF AZIRIDINES TO KETENIMINES, Journal of organic chemistry, 63(1), 1998, pp. 17-20
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
1
Year of publication
1998
Pages
17 - 20
Database
ISI
SICI code
0022-3263(1998)63:1<17:RCOATK>2.0.ZU;2-9
Abstract
The Lewis acid-catalyzed addition of aziridines to ketenimines gave su bstituted pyrrolidonimines in 47-87% yields. The hard Lewis acid LiClO 4 proved to be superior to the soft [(PhCN)(2)PdCl2], affording higher yields under milder conditions. The reaction is regioselective and oc curs with complete stereoselectivity using [(PhCN)(2)PdCl2] and with a small amount of racemization in the case of LiClO4.