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Paper | Regular issue | Vol 65, No. 12, 2005, pp.2871-2884
Published online, 4th October, 2005
DOI: 10.3987/COM-05-10508
Stereoselective Functionalization of Alkenyl-β-lactams

Luigino Troisi,* Emanuela Pindinelli, Luisella De Vitis, Catia Granito, and Ludovico Ronzini

*Department of Sciences and Biological and Environmental Technologies, University of Lecce, Via Prov.le Lecce-Monteroni, 73100 Lecce, Italy

Abstract

Alkenyl-β-lactams, obtained by palladium-catalyzed [2+2] cycloaddition of imines with allyl halides, were functionalized in a stereoselective way by a simple deprotonation with LDA, and subsequent capture of the formed carbanion by various electrophiles. Alkyl, hydroxy and epoxy functionalities were inserted exclusively at the C-3 carbon atom of the β-lactamic system, without performing new cyclizations. High stereoselectivity was noticed with the quenching taking place preferentially at the Cα with respect to the Cγ carbon atom of the allylic moiety of the azetidinyl anion generated by deprotonation.