Sequential allylic C-H amination/vinylic C-H arylation: A strategy for unnatural amino acid synthesis from α-Olefins

Chao Jiang, Dustin J. Covell, Antonia F. Stepan, Mark S. Plummer, M. Christina White

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)1386-1389
Number of pages4
JournalOrganic Letters
Volume14
Issue number6
DOIs
StatePublished - Mar 16 2012

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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