Synthesis of bis-armed amino acid derivatives via the alkylation of ethyl isocyanoacetate and the Suzuki-Miyaura cross-coupling reaction.
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.
Kotha
S
S
Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai, India. srk@chem.iitb.ac.in
Shah
V R
VR
Halder
S
S
Vinodkumar
R
R
Lahiri
K
K
D000085:Acetates / Q000737:chemistry; D000478:Alkylation; D024322:Amino Acids, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D000600:Amino Acids, Dicarboxylic / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry; D002384:Catalysis; D010165:Palladium / Q000737:chemistry; D010649:Phenylalanine / Q000031:analogs & derivatives / Q000737:chemistry
D000085:Acetates; D024322:Amino Acids, Aromatic; D000600:Amino Acids, Dicarboxylic; D001896:Boron Compounds; D010649:Phenylalanine; D010165:Palladium; C007170:cyanoacetic acid; C033685:4-boronophenylalanine