ol0260472_si_001.pdf (185.75 kB)
Samarium(II)-Mediated Reactions of γ,δ-Unsaturated Ketones. Cyclization and Fragmentation Processes
journal contribution
posted on 2002-06-19, 00:00 authored by Thomas K. Hutton, Kenneth Muir, David J. ProcterOn treatment with samarium(II) iodide, γ,δ-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.