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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11587/331854
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