Atroposelective construction of axially chiral enamides via N-allylic alkylation

Herein, we report the catalytic asymmetric synthesis of a unique family of axially chiral enamides in good yields with excellent enantioselectivities under mild conditions. These new axially chiral compounds feature a flexible skeleton and a high degree of rotational freedom, which raises difficulties for enantiocontrol. A mechanism model is proposed to interpret the stereoselectivity, in which both the steric difference of the ortho substituents and the pi-pi stacking interaction may contribute to the stereo-control.

Automated summary

In this study, a unique family of axially chiral enamides was synthesized catalytically with good yields and excellent enantioselectivities under mild conditions. These new compounds possess a flexible structure and a high degree of rotational freedom, which introduces challenges for enantiocontrol. A proposed mechanism model suggests that both the steric difference of the ortho substituents and the pi-pi stacking interaction may contribute to the stereo-control.