Stereocontrolled synthesis of fluorine-containing functionalized β-lactam derivatives through cross-metathesis reactions

Abstract

Functionalized β-lactams and their derivatives have generated increasing interest in medicinal chemistry over the last decades. Because of their pharmacological potential the chemistry of fluorinated β-lactams and β-amino acids is considered to be an expanding research field. The stereocontrolled synthesis of various fluorine-containing acylic β-lactams has been accomplished from some readily available unsaturated bicyclic β-lactam isomers. The synthetic strategy was based on ring-opening metathesis of unsaturated bicyclic azetidinones followed by cross-metathesis with fluorine-containing olefins. The cross-metathesis transformations, performed under various conditions with the aim of studying chemodiscrimination of the olefin bonds, resulted in the corresponding functionalized β-lactam derivatives.