%0 Journal Article %A Hutton, Thomas K. %A Muir, Kenneth %A Procter, David J. %D 2002 %T Samarium(II)-Mediated Reactions of γ,δ-Unsaturated Ketones. Cyclization and Fragmentation Processes %U https://acs.figshare.com/articles/journal_contribution/Samarium_II_-Mediated_Reactions_of_-Unsaturated_Ketones_Cyclization_and_Fragmentation_Processes/3742965 %R 10.1021/ol0260472.s001 %2 https://ndownloader.figshare.com/files/5834796 %K functionalized syn %K reaction conditions %K cyclopentanol products %K trig cyclization %K samarium %K iodide %K Fragmentation Processes %K Mechanistic studies %K HMPA %K fragmentation reaction %X On 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. %I ACS Publications