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Clayden J, Stimson CC, Keenan M, et al. Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums. Chem Commun (Camb). 2003;(2):228-9doi: 10.1039/b310963a.
Clayden, J., Stimson, C. C., Keenan, M., & Wheatley, A. E. (2004). Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums. Chemical communications (Cambridge, England), (2), 228-9. https://doi.org/10.1039/b310963a
Clayden, Jonathan, et al. "Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums." Chemical communications (Cambridge, England) vol. ,2 (2004): 228-9. doi: https://doi.org/10.1039/b310963a
Clayden J, Stimson CC, Keenan M, Wheatley AE. Fast racemisation and slow epimerisation of laterally lithiated amides: stereochemical evidence for the mechanism of inversion of amide-substituted benzyllithiums. Chem Commun (Camb). 2004 Jan 21;(2):228-9. doi: 10.1039/b310963a. Epub 2003 Dec 05. PMID: 14737562.
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Chem Commun (Camb). 2004 Jan 21;(2):228-9. doi: 10.1039/b310963a. Epub 2003 Dec 05.

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

Chemical communications (Cambridge, England)

Jonathan Clayden, Christopher C Stimson, Martine Keenan, Andrew E H Wheatley

Affiliations

  1. Department of Chemistry, University of Manchester, Oxford Road, Manchester, UKM13 9PL. [email protected]

PMID: 14737562 DOI: 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.

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