Journal
CHEMICAL COMMUNICATIONS
Volume -, Issue 20, Pages 2582-2583Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b308029c
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Substituted acrylamide derivatives of benzylamine are lithiated alpha 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 beta-electron withdrawing group, 4-exo-trig cyclisation to a beta-lactam.
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