title: Samarium(II)-mediated reactions of gamma,delta-unsaturated ketones. Cyclization and fragmentation processes.
abstract: [reaction: see text] On treatment with samarium(II) iodide, gamma,delta-unsaturated ketones undergo very different processes depending upon the nature of the reaction conditions. Employing samarium(II) iodide and MeOH, functionalized syn-cyclopentanol products are obtained stereoselectively. Mechanistic studies suggest that this cyclization occurs via a sequential reduction/intramolecular aldol reaction. With samarium(II) iodide and HMPA, products of a 4-exo-trig cyclization and of an interesting fragmentation reaction are observed.
authors.affiliation: Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK.
authors.forename: Thomas K
authors.initials: TK
authors.lastname: Hutton
authors.forename: Kenneth
authors.initials: K
authors.lastname: Muir
authors.forename: David J
authors.initials: DJ
authors.lastname: Procter