Tetrahedron Letters p. 3115 - 3118 (1980)
Update date:2022-08-05
Topics:
Gawley, Robert E.
Termine, Enrico J.
Aube, Jeffrey
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.
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