Stereoselective synthesis of 3,4-diaryl β-lactams

Novel 3,4-diaryl beta-lactams were prepared with high stereoselectivity in an efficient manner by a palladium-catalyzed [2+2] carborrylative cycloaddition of benzyl halides with heteroarylidene amines. The type of alkyl group linked to the nitrogen atom influences the reaction's stereoselectivity. Moreover, using chiral imines, separable diastereomeric mixtures of chiral 3,4-diaryl-beta-lactams were isolated with good yields and high trans diastereoselections. (C) 2009 Elsevier Ltd. All rights reserved.