Synthesis of tertiary cyclobutanols through stereoselective ring expansionof oxaspiropentanes induced by Grignard reagents

Authors
Bernard, AM Floris, C Frongia, A Piras, PP
Citation
Am. Bernard et al., Synthesis of tertiary cyclobutanols through stereoselective ring expansionof oxaspiropentanes induced by Grignard reagents, TETRAHEDRON, 56(26), 2000, pp. 4555-4563
Citations number
45
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
26
Year of publication
2000
Pages
4555 - 4563
Database
ISI
SICI code
0040-4020(20000623)56:26<4555:SOTCTS>2.0.ZU;2-O
Abstract
The stereoselectivity of the ring expansion of oxaspiropentanes to cyclobut anols induced by Grignard reagents has been studied. It has been found that the reaction occurs through the intermediacy of a cyclobutanone, formed st ereospecifically, whereas the attack of the Grignard reagent on the carbony l group of the cyclobutanone is stereospecific only in the case of the oxas piropentanes derived from aldehydes. (C) 2000 Elsevier Science Ltd. All rig hts reserved.