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Tandem‐Selective Bond Cleavage of the Lactam Nucleus and Michael Reaction
Author(s) -
De Vitis Luisella,
Troisi Luigino,
Granito Catia,
Pindinelli Emanuela,
Ronzini Ludovico
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600597
Subject(s) - chemistry , nucleophile , reactivity (psychology) , lactam , isomerization , cleavage (geology) , ring (chemistry) , michael reaction , bond cleavage , tandem , medicinal chemistry , stereochemistry , methanol , organic chemistry , catalysis , medicine , materials science , alternative medicine , geotechnical engineering , pathology , fracture (geology) , engineering , composite material
The reactivity of the β‐lactam ring towards nucleophiles has been investigated. Ring‐opening reactions were performed on 3‐allyl‐β‐lactams with CH 3 O – /CH 3 OH 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)