Copper-catalyzed [3 + 1] cyclization of cyclopropenes/diazo compounds and bromodifluoroacetamides: facile synthesis of α,α-difluoro-β-lactam derivatives
Mengru Zhang, Hexin Li, Jinbo Zhao, Yan Li, Qian Zhang
Abstract
We have developed a novel copper-catalyzed cyclization of cyclopropenes/diazo compounds and bromodifluoroacetamides, efficiently synthesizing a series of α,α-difluoro-β-lactams in moderate to excellent yields under mild reaction conditions. This reaction represents the first example of [3 + 1] cyclization for the synthesis of β-lactams utilizing a metal carbene intermediate as the C1 synthon.
Topics & Concepts
DiazoSynthonChemistryCatalysisCarbeneCombinatorial chemistryLactamCopperMedicinal chemistryOrganic chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry