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

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

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

22 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)228-229
Number of pages2
JournalChemical Communications
Volume10
Issue number2
Early online date5 Dec 2003
DOIs
Publication statusPublished - 21 Jan 2004

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