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EnglishThe 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.
| Titolo: | Tandem-selective Bond Cleavage of the Lactam Nucleus and Michael Reaction |
| Autori: | |
| Data di pubblicazione: | 2007 |
| Rivista: | |
| 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. |
| Handle: | http://hdl.handle.net/11587/108834 |
| Appare nelle tipologie: | Articolo pubblicato su Rivista |
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