Stereospecific Intramolecular Arylation of 2- and 3-Pyridyl Substituted Alkylamines via Configurationally Stable α-Pyridyl Organolithiums

Julien Maury, Wojciech Zawodny, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

5 Citations (Scopus)
235 Downloads (Pure)

Abstract

Treatment of N'-aryl urea derivatives of enantiomerically-enriched α-(2-pyridyl) and α-(3-pyridyl)alkylamines with base leads to the migration of the N'-aryl substituent from N to C in a 'non-classical' intramolecular nucleophilic aro-matic substitution reaction. Both electron-rich and electron-poor rings migrate successfully. A new quaternary stereo-genic centre is formed adjacent to the pyridine ring with high stereospecificity, even when the intermediate anion is a presumably planar 2-picolyllithium. Base hydrolysis of the urea gives enantiomerically enriched α-pyridylalkylamines.
Original languageEnglish
Pages (from-to)472-475
Number of pages4
JournalOrganic Letters
Volume19
Issue number3
Early online date18 Jan 2017
DOIs
Publication statusPublished - 3 Feb 2017

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