A novel and efficient synthetic method for preparing in high stereoselectivity beta-lactams poly-functionalized is reported. A palladium-catalyzed [2+2] carbonylative cycloaddition of simple allyl halides and imines affords 2-azetidinones having alkyl or aryl substituents at the heterocyclic nitrogen atom, aryl or heteroaryl moiety linked at the C-4 carbon, and alkenyl groups beared to the C-3 carbon. Moreover, through the formation of a stable carbanion at the C-3 and the C-4, it is possible to further functionalize these latter positions with various electrophiles inserting, thus, more akyl groups or alcoholic and epoxidic functions in the azetidinone ring.
Properties, Synthesis and Functionalizations of beta-Lactams
TROISI, Luigino;GRANITO, Catia;PINDINELLI, EMANUELA
2004-01-01
Abstract
A novel and efficient synthetic method for preparing in high stereoselectivity beta-lactams poly-functionalized is reported. A palladium-catalyzed [2+2] carbonylative cycloaddition of simple allyl halides and imines affords 2-azetidinones having alkyl or aryl substituents at the heterocyclic nitrogen atom, aryl or heteroaryl moiety linked at the C-4 carbon, and alkenyl groups beared to the C-3 carbon. Moreover, through the formation of a stable carbanion at the C-3 and the C-4, it is possible to further functionalize these latter positions with various electrophiles inserting, thus, more akyl groups or alcoholic and epoxidic functions in the azetidinone ring.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
