DEPROTONATIONS, CONJUGATE ADDITIONS, AND ENOLATE TRAPPING OF OXIME ETHERS AND DIMETHYLHYDRAZONES USING KDA. THE EFFECT OF DIISOPROPYLAMINE ON ENOLATE TRAPPING.

Article abstract of DOI:10.1016/S0040-4039(00)77423-5

Potassium diisopropylamide (KDA) has been used to efficiently generate the anions of oxime ethers and dimethylhydrazones.As a deprotonating agent, KDA is superior to BuLi and LDA.The corresponding cuprates are extremly oxygen sensitive, but undergo 1,4-addition with cyclohexenone, and the resulting potassium enolates can be trapped with aqueous buffer or ClSiMe3.Attempted trapping with either AC2O or AcCl in the presence of diisopropylamine fails.