Highly Regio- and Diastereoselective Palladium-Catalyzed Allylic Substitution. Synthesis of 3-(2-aminobutylidene)-4-arylazetidin-2-ones

The palladium-catalyzed benzylamine attack to a particular allylic moiety, the 3-alkenyl-3-bromo-azetidin-2-one is herein reported. This reaction shows interesting mechanistic aspects and allows to introduce in one step and under high regio- and stereocontrol the amino function in the C3 side chain of the non conventional beta-lactams, thus offering the opportunity for designing new potential glutamine syntethase inhibitors, such as Tabtoxin analogues.