Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums |
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| Authors: | Clayden Jonathan Stimson Christopher C Keenan Martine Wheatley Andrew E H |
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| Affiliation: | Department of Chemistry, University of Manchester, Oxford Road, Manchester, UKM13 9PL. j.p.clayden@man.ac.uk |
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| 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. |
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