Stereoselective synthesis of β-alkylated α-amino acids via palladium-catalyzed alkylation of unactivated methylene C(sp3)-H Bonds with Primary Alkyl Halides

Shu Yu Zhang, Qiong Li, Gang He, William A. Nack, Gong Chen

Research output: Contribution to journalArticlepeer-review

240 Scopus citations

Abstract

We report a new set of reactions based on the Pd-catalyzed alkylation of methylene C(sp3)-H bonds of aliphatic quinolyl carboxamides with α-haloacetate and methyl iodide and applications in the stereoselective synthesis of various β-alkylated α-amino acids. These reactions represent the first generally applicable method for the catalytic alkylation of unconstrained and unactivated methylene C-H bonds with high synthetic relevance. When applied with simple isotope-enriched reagents, they also provide a convenient and powerful means to site-selectively incorporate isotopes into the carbon scaffolds of amino acid compounds.

Original languageEnglish (US)
Pages (from-to)12135-12141
Number of pages7
JournalJournal of the American Chemical Society
Volume135
Issue number32
DOIs
StatePublished - Aug 14 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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