Stereoselective Synthesis of trans β-Lactams through Iridium-Catalyzed Reductive Coupling of Imines and Acrylates

JA Townes, MA Evans, J Queffelec, SJ Taylor…

Index: Townes, Jennifer A.; Evans, Michael A.; Queffelec, Jerome; Taylor, Steven J.; Morken, James P. Organic Letters, 2002 , vol. 4, # 15 p. 2537 - 2540

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Citation Number: 56

Abstract

Iridium-catalyzed reductive coupling of acrylates and imines provides trans β-lactams with high diastereoselection. The optimal catalyst allows for the synthesis of trans β-lactams bearing aromatic, alkenyl, and alkynyl side chains. This reaction appears to proceed through a reductive Mannich addition-cyclization mechanism. Examination of substituent effects reveals a linear Hammett correlation for both the N-aryl group on the imine and the aryloxy ...