Highly regio- and diastereoselective palladium-catalyzed allylic substitution. Synthesis of 3-(2-aminobutylidene)4-arylazetidin-2-ones

摘要

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