title: Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins.
abstract: 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 α- and β-homophenylalanine precursors from commodity α-olefins and readily available aryl boronic acids. General routes to enantiopure amino acid esters and densely functionalized homophenylalanine derivatives are demonstrated.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
authors.forename: Chao
authors.initials: C
authors.lastname: Jiang
authors.forename: Dustin J
authors.initials: DJ
authors.lastname: Covell
authors.forename: Antonia F
authors.initials: AF
authors.lastname: Stepan
authors.forename: Mark S
authors.initials: MS
authors.lastname: Plummer
authors.forename: M Christina
authors.initials: MC
authors.lastname: White
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000596:Amino Acids