2-Aryltetrahydropyridines formed by anionic cyclization or ring-closing metathesis were converted to their N′-aryl urea derivatives. Depending on the position of the unsaturation within the tetrahydropyridine ring, metalation by deprotonative lithiation or carbolithiation led to migration of the N′-aryl substituent to the 2- or 6-position via intramolecular nucleophilic attack of a benzylic organolithium on the aryl ring. The products are a range of 2,2-, 2,2,3-, and 2,6-polysubstituted piperidine derivatives. Related chemistry was observed in pyrroline homologues.
|Number of pages||4|
|Early online date||18 Feb 2015|
|Publication status||Published - 6 Mar 2015|
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry