Palladium-catalyzed β-C(sp3)-H arylation of phthaloyl alanine with hindered aryl iodides: Synthesis of complex β-aryl α-amino acids

Xuekai Zhang, Gang He, Gong Chen

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

An efficient protocol for palladium-catalyzed β-C(sp3)-H arylation of aliphatic carboxamides equipped with a 2-(2-pyridyl) ethylamine (PE) auxiliary was developed. The PE auxiliary is uniquely effective at facilitating the arylation of primary C(sp3)-H bonds with sterically hindered aryl iodides. A variety of aryl iodides bearing alkoxyl, carbonyl, nitro and halogen groups on the ortho position can react with the PE-coupled phthaloyl alanine substrate in moderate to excellent yield. These reactions offer a useful solution for preparing complex β-aryl α-amino acid products from readily accessible starting materials.

Original languageEnglish (US)
Pages (from-to)5511-5515
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number24
DOIs
StatePublished - Jan 1 2016

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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