Issue 20, 2003
From the journal:

Chemical Communications

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

Jonathan Clayden,*a   David W. Watson,a   Madeleine Helliwella  and  Mark Chambersb  

* Corresponding authors

a Department of Chemistry, University of Manchester, Oxford Road, Manchester, UK

b Merck Sharp and Dohme Research Laboratories, Neuroscience Research Centre, Terlings Park, Harlow, Essex, UK

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.

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

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Article information

DOI
https://doi.org/10.1039/B308029C
Article type
Communication
Submitted
14 Jul 2003
Accepted
22 Aug 2003
First published
18 Sep 2003

Chem. Commun., 2003, 2582-2583

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

J. Clayden, D. W. Watson, M. Helliwell and M. Chambers, Chem. Commun., 2003, 2582 DOI: 10.1039/B308029C

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