Tandem-Selective Bond Cleavage of the Lactam Nucleus and Michael Reaction

Autor:	Catia Granito, Emanuela Pindinelli, Luisella De Vitis, Luigino Troisi, Ludovico Ronzini
Přispěvatelé:	DE VITIS, Luisella, Troisi, Luigino, Granito, Catia, Pindinelli, Emanuela, Ronzini, Ludovico
Rok vydání:	2007
Předmět:	Cleavage reaction Amino esters Chemistry Stereochemistry Organic Chemistry Ring (chemistry) chemistry.chemical_compound Nucleophile Michael addition Lactam polycyclic compounds Michael reaction Reactivity (chemistry) Amino ester Physical and Theoretical Chemistry Isomerization Bond cleavage
Zdroj:	European Journal of Organic Chemistry. 2007:356-362
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.200600597
Popis:	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. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b26e5e78f2529a0f2fff7d50b61f2a6d https://doi.org/10.1002/ejoc.200600597 Zobrazit plný text záznamu Plný text