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

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journal contribution
posted on 2016-02-21, 17:29 authored by Chao Jiang, Dustin J. Covell, Antonia F. Stepan, Mark S. Plummer, M. Christina White
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.