Intermolecular Dearomatising Addition of Organolithium Compounds to N??Benzoylamides of 2, 2, 6, 6??Tetramethylpiperidine

J Clayden, YJY Foricher, HK Lam

Index: Clayden, Jonathan; Foricher, Yann J. Y.; Lam, Ho Kam European Journal of Organic Chemistry, 2002 , # 21 p. 3558 - 3565

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Citation Number: 12

Abstract

Abstract N-Benzoylamides of 2, 2, 6, 6-tetramethylpiperidine are not ortholithiated by organolithium compounds but instead undergo nucleophilic addition of the organolithium compound to the aromatic ring in the manner of a conjugate addition. The resulting dearomatised enolates may be protonated or alkylated, and yield substituted cyclohexadienes in yields of up to 76%. Deprotection of the piperidine ring is possible ...