The reactivity of the β-lactam ring towards nucleophiles has been investigated. Ring-opening reactions were performed on 3-allyl-β-lactams with CH3O–/CH3OH at room temperature and/or reflux. Lactam nucleus isomerization followed by N1–C2 bond cleavage and methanol Michael addition afforded substituted amino esters. The reactivity of the four-membered ring towards nucleophiles was found to depend on the substituents at the lactamic nitrogen and the C3 and C4 atoms. The ring-opening path is highlighted in this report.
Tandem-selective Bond Cleavage of the Lactam Nucleus and Michael Reaction
DE VITIS, LUISELLA;TROISI, Luigino;GRANITO, Catia;PINDINELLI, EMANUELA;RONZINI, Ludovico
2007-01-01
Abstract
The reactivity of the β-lactam ring towards nucleophiles has been investigated. Ring-opening reactions were performed on 3-allyl-β-lactams with CH3O–/CH3OH at room temperature and/or reflux. Lactam nucleus isomerization followed by N1–C2 bond cleavage and methanol Michael addition afforded substituted amino esters. The reactivity of the four-membered ring towards nucleophiles was found to depend on the substituents at the lactamic nitrogen and the C3 and C4 atoms. The ring-opening path is highlighted in this report.File in questo prodotto:
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