title: Intramolecular ene reaction of epoxyallylsilanes: synthesis of allyl- and vinylsilane-functionalized cyclohexanols.
abstract: [reaction: see text] Epoxyallylsilanes bearing the bulky tert-butyldiphenylsilyl group undergo an uncommon tandem rearrangement-cyclization process upon treatment with Lewis acids. Two pathways for the carbonyl ene reaction are observed: one leading to allylsilane-cyclohexanols when the epoxyallylsilane (28-31) is nonsubstituted, 2-, or 4-monosubstituted and other leading to vinylsilane-cyclohexanols when the epoxyallylsilane (24-27) is 2,4-disubstituted or trisubstituted. An explanation for the observed regio- and stereoselectivity is advanced and a reliable mechanism proposed.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, C/Dr Mergelina s/n, 47011 Valladolid, Spain.
authors.forename: Asunción
authors.initials: A
authors.lastname: Barbero
authors.forename: Pilar
authors.initials: P
authors.lastname: Castreño
authors.forename: Gloria
authors.initials: G
authors.lastname: Fernández
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Pulido