Abstract
Cycloalkenones were found to react with α-lithiated diethyl (phenylselanyl)methylphosphonate preferentially or exclusively at the carbonyl group giving 1,2-adducts. When complexes of cycloalkenones with aluminum tris(2,6-diphenylphenoxide) were used for this reaction, regioselective 1,4-addition was observed. Upon oxidation the thus-formed 1,4-adducts gave the corresponding 3-(phosphorylmethyl)cycloalk-2-enones. An alternative approach to the latter compounds involved 1,4-addition of diethyl lithiomethylphosphonate to 2-sulfinylcycloalk-2-enones followed by sulfoxide elimination.
Key words
conjugate addition - cycloalkenones - α-phosphonate carbanions - 3-phosphorylcycloalk-2-enones
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