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

• DOI: 10.1021/ol300063t
• Publication Date: 2012-02-24T13:35:06Z
• Authors: Chao Jiang; Dustin J. Covell; Antonia F. Stepan; Mark S. Plummer; M. Christina White
• Keywords: Enantiopure drug; Tandem

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