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 under acidic conditions. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
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Clayden et al. (2002) studied this question.