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. β-lactams
featuring two contiguous stereocenters at Cβ and the β
substituent can be obtained in good yield with excellent enantioselectivity.
Mechanistic studies indicate that a nucleophilic addition of the alkyl
radical to CuII-coordinated alkene is the enantio-determining
step.