REGIO-CONTROLLED IODOAMINOCYCLIZATION REACTION OF AN AMBIDENT NUCLEOPHILE MEDIATED BY LIAL(OT-BU)(4)

Authors
KITAGAWA O FUJITA M LI H TAGUCHI T
Citation
O. Kitagawa et al., REGIO-CONTROLLED IODOAMINOCYCLIZATION REACTION OF AN AMBIDENT NUCLEOPHILE MEDIATED BY LIAL(OT-BU)(4), Tetrahedron letters, 38(4), 1997, pp. 615-618
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
4
Year of publication
1997
Pages
615 - 618
Database
ISI
SICI code
0040-4039(1997)38:4<615:RIROAA>2.0.ZU;2-E
Abstract
A new and general method of iodine-mediated cyclization reactions of u nsaturated carbamates, ureas and amides which gives N-cyclized product s as a single regio-isomer was achieved. The present reaction proceeds in good yield through regio-control of an ambident nucleophile by LiA l(Ot-Bu)(4), and the regio-control (N-attack vs O-attack) was also fou nd to be remarkably affected by the additive employed. (C) 1997, Elsev ier Science Ltd. All rights reserved.