Kinetic enolate formation by lithium arylamide: Effects of basicity on selectivity

L Xie, K Vanlandeghem, KM Isenberger…

Index: Xie, Linfeng; Vanlandeghem, Keith; Isenberger, Kurt M.; Bernier, Carolyn Journal of Organic Chemistry, 2003 , vol. 68, # 2 p. 641 - 643

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Citation Number: 24

Abstract

Five ketones R1COCH2R2 (1a-e) were enolized in tetrahydrofuran solvent employing lithium arylamides with different electron-withdrawing and-donating substituents on the phenyl ring (4a-e). Enolate selectivity is unaffected by a moderate electron-releasing or- withdrawing group, but significantly enhanced by strong electron-withdrawing substituents to yield predominantly Z-enolate. Outstanding selectivity was achieved with lithium ...

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