[1,4]-SPh shift cyclisations or [1,2]-SPh-cyclisations as alternative cascade sequences for stereocontrolled synthesis of substituted tetrahydrofurans

Citation
J. Eames et al., [1,4]-SPh shift cyclisations or [1,2]-SPh-cyclisations as alternative cascade sequences for stereocontrolled synthesis of substituted tetrahydrofurans, SYNLETT, (8), 1999, pp. 1215-1218
Citations number
14
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
8
Year of publication
1999
Pages
1215 - 1218
Database
ISI
SICI code
0936-5214(199908):8<1215:[SCO[A>2.0.ZU;2-K
Abstract
Treatment of 4-phenylsulfanyl-1,5,7-triols with TsCl in pyridine gives subs tituted tetrahydrofurans by [1,4]-SPh participation via a five membered sul fonium salt and then capture by a tethered nucleophile. Acid catalysed rear rangement gives other THFs by [1,2]-SPh migration and cyclisations.