2,2- and 2,6-diarylpiperidines by aryl migration within lithiated urea derivatives of tetrahydropyridines
Research output: Contribution to journal › Article › peer-review
Authors
Colleges, School and Institutes
External organisations
- University of Manchester
- AstraZeneca
Abstract
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.
Details
Original language | English |
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Pages (from-to) | 1236-1239 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 17 |
Issue number | 5 |
Early online date | 18 Feb 2015 |
Publication status | Published - 6 Mar 2015 |