Enantioselective Alkylamination of Unactivated Alkenes under Copper Catalysis

An enantioselective addition reaction of various alkyl groups to unactivated internal alkenes under Cu catalysis has been developed. The reaction uses amide-linked aminoquinoline as the directing group, 4-alkyl Hantzsch esters as the donor of alkyl radicals, and rarely used biaryl diphosphine oxide as a chiral ligand beta-lactams featuring two contiguous stereocenters at C beta and the beta substituent can be obtained in good yield with excellent enantioselectivity. Mechanistic studies indicate that a nucleophilic addition of the alkyl radical to Cu-II-coordinated alkene is the enantio-determining step.

Automated summary

An enantioselective addition reaction of various alkyl groups to unactivated internal alkenes under Cu catalysis has been developed, leading to high yields of β-lactams featuring two contiguous stereocenters with excellent enantioselectivity. Mechanistic studies suggest that a nucleophilic addition of the alkyl radical to Cu-II-coordinated alkene is the enantio-determining step.