A STEREOSELECTIVE INTRAMOLECULAR RETRO-ENE REACTION CATALYZED BY ALUMINUM-CHLORIDE

Authors
BODAJLA M JONES GR RAMSDEN CA
Citation
M. Bodajla et al., A STEREOSELECTIVE INTRAMOLECULAR RETRO-ENE REACTION CATALYZED BY ALUMINUM-CHLORIDE, Tetrahedron letters, 38(14), 1997, pp. 2573-2576
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
14
Year of publication
1997
Pages
2573 - 2576
Database
ISI
SICI code
0040-4039(1997)38:14<2573:ASIRRC>2.0.ZU;2-K
Abstract
Reaction of 5-(2-naphthalenol)-1-pentenes with I(III) reagents results in nucleophilic substitution at C-1 rather than [4+2] intramolecular ionic cycloaddition of the proposed intermediate arenoxenium cations. Treatment of the same precursors with aluminium chloride results in a stereoselective intramolecular cyclisation to spiroketones. Evidence t hat the mechanism of formation involves a cyclic aluminium intermediat e is presented. (C) 1997 Elsevier Science Ltd.