Sequential Allylic C-H Amination/Vinylic C-H Arylation: A Strategy for Unnatural Amino Acid Synthesis from α-Olefins

Tandem reaction sequences that selectively convert multiple C-H bonds of abundant hydrocarbon feedstocks to functionalized materials enable rapid buildup of molecular complexity in an economical way. A tandem C-H amination/vinylic C-H arylation reaction sequence is described under Pd(II)/sulfoxide-catalysis that furnishes a wide range of alpha- and beta-homophenylalanine precursors from commodity alpha-olefins and readily available aryl boronic acids. General routes to enantiopure amino acid esters and densely functionalized homophenylalanine derivatives are demonstrated.