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.
Stereoselective Functionalization of Alkenyl-b-Lactams.
TROISI, Luigino;PINDINELLI, EMANUELA;DE VITIS, LUISELLA;GRANITO, Catia;RONZINI, Ludovico
2005-01-01
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.File in questo prodotto:
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