Issue 2, 2004

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

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

Article information

Article type
Communication
Submitted
09 Sep 2003
Accepted
17 Nov 2003
First published
05 Dec 2003

Chem. Commun., 2004, 228-229

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements