β-Lactams or γ-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives

Jonathan Clayden*, David W. Watson, Madeleine Helliwell, Mark Chambers

*Corresponding author for this work

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

30 Citations (Scopus)

Abstract

Substituted acrylamide derivatives of benzylamine are lithiated α to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a β-electron withdrawing group, 4-exo-trig cyclisation to a β-lactam.

Original languageEnglish
Pages (from-to)2582-2583
Number of pages2
JournalChemical Communications
Volume9
Issue number20
Early online date18 Sep 2003
DOIs
Publication statusPublished - 21 Oct 2003

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