pH-Dependent chemoselective synthesis of alpha-amino acids. Reductive amination of alpha-keto acids with ammonia catalyzed by acid-stable iridium hydride complexes in water.
An acid-stable hydride complex [Cp*IrIII(bpy)H]+ {1, Cp* = eta5-C5Me5, bpy = 2,2'-bipyridine} serves as the active catalyst for the highly chemoselective synthesis of alpha-amino acids by reductive amination of alpha-keto acids with aqueous NH3 and HCOO- in water at pH 5-8. pH-dependent catalytic 15N- and 2H-double-labeling has also been accomplished by using 15NH3 and DCOONa, which are ideal amine and hydride ion sources, respectively.
Ogo
Seiji
S
Department of Material and Life Science, Graduate School of Engineering, Osaka University, PRESTO & CREST, Japan Science and Technology Agency (JST), Suita, Osaka 565-0871, Japan. ogo@ap.chem.eng.osaka-u.ac.jp
Uehara
Keiji
K
Abura
Tsutomu
T
Fukuzumi
Shunichi
S
D000586:Amination; D000596:Amino Acids / Q000138:chemical synthesis*; D000641:Ammonia / Q000737:chemistry*; D002384:Catalysis; D006863:Hydrogen-Ion Concentration; D007495:Iridium / Q000737:chemistry*; D007651:Keto Acids / Q000737:chemistry*; D010084:Oxidation-Reduction; D014867:Water / Q000737:chemistry
D000596:Amino Acids; D007651:Keto Acids; D014867:Water; D007495:Iridium; D000641:Ammonia