title: Stereospecific Intramolecular Arylation of 2- and 3-Pyridyl Substituted Alkylamines via Configurationally Stable α-Pyridyl Organolithiums.
abstract: Treatment of N'-aryl urea derivatives of enantiomerically enriched α-(2-pyridyl) and α-(3-pyridyl)alkylamines with a base leads to the migration of the N'-aryl substituent from N to C in a 'nonclassical' intramolecular nucleophilic aromatic substitution reaction. Both electron-rich and -poor rings migrate successfully. A new quaternary stereogenic center 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.
authors.affiliation: School of Chemistry, University of Manchester , Oxford Road, Manchester M13 9PL, U.K.|School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, U.K.
authors.forename: Julien
authors.initials: J
authors.lastname: Maury
authors.affiliation: School of Chemistry, University of Manchester , Oxford Road, Manchester M13 9PL, U.K.
authors.forename: Wojciech
authors.initials: W
authors.lastname: Zawodny
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, U.K.
authors.forename: Jonathan
authors.identifier: 0000-0001-5080-9535
authors.initials: J
authors.lastname: Clayden