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Issue 2, 2004
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Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums

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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.

Graphical abstract: Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums

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Publication details

The article was received on 09 Sep 2003, accepted on 17 Nov 2003 and first published on 05 Dec 2003


Article type: Communication
DOI: 10.1039/B310963A
Citation: Chem. Commun., 2004, 228-229
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    Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums

    J. Clayden, C. C. Stimson, M. Keenan and A. E. H. Wheatley, Chem. Commun., 2004, 228
    DOI: 10.1039/B310963A

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