Tetrahedron Letters

Deprotonations, conjugate additions, and enolate trapping of oxime ethers and dimethylhydrazones using KDA: The effect of diisopropylamine on enolate trapping

RE Gawley, EJ Termine, J Aube

Index: Gawley, Robert E.; Termine, Enrico J.; Aube, Jeffrey Tetrahedron Letters, 1980 , vol. 21, p. 3115 - 3118

Full Text: HTML

Citation Number: 23

Abstract

Abstract 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 extremely oxygen sensitive, but undergo 1, 4- addition with cyclohexenone, and the resulting potassium enolates can be trapped with aqueous buffer or ClSiMe 3. Attempted trapping with either Ac 2 O or AcCl in the presence ...