Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums
Literature Information
Jonathan Clayden, Christopher C. Stimson, Martine Keenan, Andrew E. H. Wheatley
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.
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