%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