Beta-lactams or gamma-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives |
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| Authors: | Clayden Jonathan Watson David W Helliwell Madeleine Chambers Mark |
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| Institution: | Department of Chemistry, University of Manchester, Oxford Road, Manchester, UK M13 9PL. |
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| Abstract: | 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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