New synthesis and cyclopropanation of α-phenylselanyl α,β-unsaturated ketones with non-stabilized phosphorus ylides |
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| Authors: | Sébastien Redon Francis Outurquin |
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| Institution: | Université and INSA de Rouen-C.O.B.R.A.-I.R.C.O.F., UMR 6014 CNRS, 1, rue Tesnière, 76131 Mont-Saint-Aignan cedex, France |
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| Abstract: | A general method for the preparation of α-phenylselanyl enones is described. Phosphorus ylides react with these α-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. |
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| Keywords: | Selenium α-Phenylselanyl enones Cyclopropane Dihydrofuran Conjugated dienes |
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