title: Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums.
abstract: Tertiary 1-naphthamides racemise much more slowly than their laterally lithiated derivatives, and the relative rates of racemisation and epimerisation of these derivatives indicate that the lithium-bearing stereogenic centre inverts via a "conducted tour" mechanism, in which the lithium cation is delivered from one face to the other by coordination to the rotating amide group.
authors.affiliation: Department of Chemistry, University of Manchester, Oxford Road, Manchester, UKM13 9PL. j.p.clayden@man.ac.uk
authors.forename: Jonathan
authors.initials: J
authors.lastname: Clayden
authors.forename: Christopher C
authors.initials: CC
authors.lastname: Stimson
authors.forename: Martine
authors.initials: M
authors.lastname: Keenan
authors.forename: Andrew E H
authors.initials: AE
authors.lastname: Wheatley