Abstract
N-Benzoylamides of 2,2,6,6-tetramethylpiperidine are not ortholithiated by organolithium compds. but instead undergo nucleophilic addn. of the organolithium compd. to the arom. ring in the manner of a conjugate addn. The resulting dearomatized 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. [on SciFinder (R)]
Original language | English |
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Pages (from-to) | 3558-3565 |
Journal | European Journal of Organic Chemistry |
DOIs | |
Publication status | Published - 2002 |
Keywords
- Lithiation (intermol. dearomatizing addn. of organolithium compds. to (benzoyl)tetramethylpiperidine derivs.); Addition reaction (nucleophilic; intermol. dearomatizing addn. of organolithium compds. to (benzoyl)tetramethylpiperidine derivs.); Crystal structure; Molecular structure (of (methoxybenzoyl)tetramethylpiperidine); Aromatization (retro; intermol. dearomatizing addn. of organolithium compds. to (benzoyl)tetramethylpiperidine derivs.)