Enantioselective sp(3) C-H alkylation of γ-butyrolactam by a chiral Ir(I) catalyst for the synthesis of 4-substituted γ-amino acids

Chem Commun (Camb). 2015 Dec 4;51(93):16660-3. doi: 10.1039/c5cc07102j. Epub 2015 Oct 1.

Abstract

Ir-catalyzed sp(3) C-H alkylation of γ-butyrolactam with alkenes was used for the highly enantioselective synthesis of 5-substituted γ-lactams, which were readily converted into chiral 4-substituted γ-amino acids. A broad scope of alkenes was amenable as coupling partners, and the alkylated product using acrylate could be transformed into the key intermediate of pyrrolam A synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Catalysis
  • Iridium / chemistry*
  • Lactams / chemistry*
  • Molecular Conformation
  • Organometallic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Lactams
  • Organometallic Compounds
  • Iridium