Tetrahedron

New synthesis and cyclopropanation of α-phenylselanyl α, β-unsaturated ketones with non-stabilized phosphorus ylides

…, S Leleu, X Pannecoucke, X Franck, F Outurquin

文献索引：Redon, Sebastien; Leleu, Stephane; Pannecoucke, Xavier; Franck, Xavier; Outurquin, Francis Tetrahedron, 2008 , vol. 64, # 39 p. 9293 - 9304

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被引用次数: 16

摘要

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.