STEREOCONTROL OF METAL-CATALYZED CYCLOADDITION OF CARBONYL YLIDE WITHN-SUBSTITUTED MALEIMIDE

Authors
SUGA H ISHIDA H IBATA T
Citation
H. Suga et al., STEREOCONTROL OF METAL-CATALYZED CYCLOADDITION OF CARBONYL YLIDE WITHN-SUBSTITUTED MALEIMIDE, Tetrahedron letters, 39(20), 1998, pp. 3165-3166
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
20
Year of publication
1998
Pages
3165 - 3166
Database
ISI
SICI code
0040-4039(1998)39:20<3165:SOMCOC>2.0.ZU;2-U
Abstract
The CuOTf (20 mol%) or CuCl-Yb(OTf)(3) (5 mol%) catalyzed decompositio n of o-(methoxycarbonyl)-alpha-diazoacetophenone in the presence of N- methylmaleimide gave 1,3-dipolar cycloadducts in an endo-selective man ner (endo : exo = 94 : 6). On the other hand, the Rh-2(OAc)(4)-catalyz ed (5 mol%) reaction gave cycloadducts with exo-selectivity (endo : ex o = 11 : 89). (C) 1998 Elsevier Science Ltd. All rights reserved.