Synthesis of bis-armed amino acid derivatives via the alkylation of ethyl isocyanoacetate and the Suzuki-Miyaura cross-coupling reaction

Amino Acids. 2007;32(3):387-94. doi: 10.1007/s00726-006-0402-2. Epub 2006 Oct 10.

Abstract

Two synthetic routes to bis-armed-alpha-amino acid derivatives are described. The first route involves alkylation of dibromo derivatives with ethyl isocyanoacetate under phase-transfer catalysis (PTC) conditions. The second route uses a palladium-mediated Suzuki-Miyaura cross-coupling reaction between a DL-4-boronophenylalanine derivative and aromatic diiodo (or dibromo) compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry
  • Alkylation
  • Amino Acids, Aromatic / chemical synthesis*
  • Amino Acids, Aromatic / chemistry
  • Amino Acids, Dicarboxylic / chemical synthesis*
  • Amino Acids, Dicarboxylic / chemistry
  • Boron Compounds / chemistry
  • Catalysis
  • Palladium / chemistry
  • Phenylalanine / analogs & derivatives
  • Phenylalanine / chemistry

Substances

  • Acetates
  • Amino Acids, Aromatic
  • Amino Acids, Dicarboxylic
  • Boron Compounds
  • Phenylalanine
  • Palladium
  • cyanoacetic acid
  • 4-boronophenylalanine