NOVEL WINDSCREEN WIPER CAVITY STRUCTURES FORMED BY THE CYCLOADDITION OF N-SUBSTITUTED ISOINDOLES ONTO MOLRAC BIS-ALKENES

Authors
MALPASS JR SUN GX FAWCETT J WARRENER RN
Citation
Jr. Malpass et al., NOVEL WINDSCREEN WIPER CAVITY STRUCTURES FORMED BY THE CYCLOADDITION OF N-SUBSTITUTED ISOINDOLES ONTO MOLRAC BIS-ALKENES, Tetrahedron letters, 39(19), 1998, pp. 3083-3086
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
19
Year of publication
1998
Pages
3083 - 3086
Database
ISI
SICI code
0040-4039(1998)39:19<3083:NWWCSF>2.0.ZU;2-X
Abstract
A strong N-substituent effect is observed in the reaction of isoindole s with cyclobutene-1,2-diesters: N-alkyloxycarbonyl derivatives react to form adducts with bent-frame stereostructures; N-alkylisoindoles pr oduce both extended-frame (stable) and bent-frame (unstable) stereoiso mers, but require high-pressure conditions (10-15 kbar); N-acyl isoind oles fail to react. Reaction of N-benzyl tetrafluoroisoindole 6c with bis-alkene 13 produced the first 'windscreen wiper' N-bridged cavity c ompound 12, the structure of which was confirmed by X-ray analysis. (C ) 1998 Elsevier Science Ltd. All rights reserved.