Towards Atropoenantiopure N–C Axially Chiral Compounds via Stereoselective C–N Bond Formation

Abstract

N–C axial chirality, although disregarded for decades, is an interesting type of chirality with appealing applications in medicinal chemistry and agrochemistry. However, atroposelective synthesis of optically pure compounds is extremely challenging and only a limited number of synthetic routes have been designed. In particular, asymmetric N-arylation reactions allowing atroposelective N–C bond forming events remain scarce, although great advances have been achieved recently. In this minireview we summarize the synthetic approaches towards synthesis of N–C axially chiral compounds via stereocontrolled N–C bond forming events. Both organo-catalyzed and metal-catalyzed transformations are described, thus illustrating the diversity and specificity of both strategies.

Keywords

• assymetric synthesis
• axial chirality
• c-n axial chirality
• hypervalent iodine
• n-c atropisomerism
• n-c axial chirality