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Stereoselective synthesis and functionalization of 4-heterosubstituted β-lactams
Authors:Luigino Troisi  Ludovico Ronzini  Catia Granito  Luisella De Vitis  Emanuela Pindinelli
Affiliation:Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali, University of Lecce, Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy
Abstract:Polyfunctionalized β-lactams were prepared with high stereoselectivity in an efficient manner. A palladium-catalyzed [2+2] carbonylative cycloaddition of allyl bromide with heteroaryliden-anilines afforded 2-azetidinones N-phenyl substituted, with an heteroaryl moiety linked at the C-4 carbon, and an alkenyl group at the C-3 carbon. The C-3 and the C-4 positions could be further functionalized inserting alkyl and hydroxyl groups in the azetidinone ring, through the generation of a stable azetidinyl anion then captured by various electrophiles.
Keywords:Alkenyl β-lactams   Electrophiles   Cabonylative cycloaddition   Stereoselectivity
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