Stereoselective synthesis of chiral α-amino-β-lactams through palladium(II)-catalyzed sequential monoarylation/amidation of C(sp(3) )-H bonds.

Research paper by Qi Q Zhang, Kai K Chen, Weihao W Rao, Yuejun Y Zhang, Fa-Jie FJ Chen, Bing-Feng BF Shi

Indexed on: 01 Nov '13Published on: 01 Nov '13Published in: Angewandte Chemie International Edition


Give Me an Ar, give Me an N! Arylation of the methyl group in a simple derivative of readily available alanine under palladium catalysis was followed by intramolecular amidation at the same position to give chiral α-amino-β-lactams with a wide range of aryl substituents (see scheme; Phth=phthaloyl). The α-amino-β-lactams were obtained in moderate to high yields with good functional-group tolerance and high diastereoselectivity.