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Intermolecular Dearomatising Addition of Organolithium Compounds to N ‐Benzoylamides of 2,2,6,6‐Tetramethylpiperidine
Author(s) -
Clayden Jonathan,
Foricher Yann J. Y.,
Lam Ho Kam
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200211)2002:21<3558::aid-ejoc3558>3.0.co;2-5
Subject(s) - chemistry , organolithium compounds , piperidine , ring (chemistry) , conjugate , alkylation , protonation , yield (engineering) , nucleophile , nucleophilic addition , organic chemistry , medicinal chemistry , intermolecular force , stereochemistry , deprotonation , catalysis , molecule , ion , mathematical analysis , materials science , mathematics , metallurgy
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)