Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums
- 5 December 2003
- journal article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 2,p. 228-229
- https://doi.org/10.1039/b310963a
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.Keywords
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