Synthesis of 4-(trimethylsilyl)-amd 4-(tributylstannyl)-2-azetidinones and some of their applications to β-lactam chemistry

Article abstract of DOI:10.1016/0040-4039(90)80147-E

Silylcupration and stannylcupration of 4-acetoxy-2-azetidinones gave the corresponding silyl- and stannyl-β-lactams. The first results on the reactivity of these products with electrophiles are reported: 4-(tributylstannyl)- 2-azetidinone undergoes the palladium catalyzed coupling with electrophiles allowing an 'umpolung' acylation of the position 4 of the β-lactam ring.