To cite this version:Sébastien Redon, Stéphane Leleu, Xavier Pannecoucke, Xavier Franck, Francis Outurquin. New synthesis and cyclopropanation of α-phenylselanyl α,β-unsaturated ketones with non-stabilized phosphorus ylides. Tetrahedron, Elsevier, 2008, 64 (39), pp.9293-9304. 10.1016/j.tet.2008 New synthesis and cyclopropanation of -phenylselanyl -
abstractA general method for the preparation of -phenylselanyl enones is described. Phosphorus ylides react with these -phenylselanyl enones in a 1,4-addition, leading to cyclopropanes and/or dihydrofurans, depending on the substitution pattern. This unusual reactivity is due to the phenylselanyl moiety, hindering the carbonyl of the enone and making it less prone to 1,2-additions or promoting conjugate addition by electronic effects.