Direct Catalytic Asymmetric α-Allylic Alkylation of Aza-aryl Methylamines by Chiral-Aldehyde-Involved Ternary Catalysis System

A ternary catalytic system comprising a chiral aldehyde, a transition metal, and a Lewis acid is rationally designed for the asymmetric alpha-allylic alkylation reaction of aza-aryl methylamines and pi-allylmetal electrophiles. Structural diversity chiral amines bearing carbon-carbon double bonds and aza-heterocycles are produced in moderate to good yields with good to excellent enantioselectivities. These products can be readily converted into other chiral amines without the loss of enantioselectivity. A reasonable reaction mechanism is proposed to illustrate the stereoselective control results.

Automated summary

A ternary catalytic system consisting of a chiral aldehyde, a transition metal, and a Lewis acid is designed for the asymmetric alpha-allylic alkylation reaction. The products are diverse chiral amines with good to excellent yields and enantioselectivities. These products can be easily converted into other chiral amines without loss of enantioselectivity.