Palladium-catalyzed tert-butoxycarbonylation of trifluoroacetimidoyl iodides.
A modification and details of the palladium-catalyzed tert-butoxycarbonylation of 2,2,2-trifluoroacetimidoyl iodides 1, which gave the iminocarboxylates 2, one of the promising precursors to fluorinated alpha-amino acids, are described. The Pd-catalyzed carbonylation reaction was remarkably promoted by the use of DMF or DMI as an additive, enough to achieve the selective formation of tert-butyl iminoesters. Nucleophilic alkylation of the imine moiety of 2 and subsequent removal of N- and O-protecting groups gave a variety of 2-substituted 2-amino-3,3,3-trifluoropropanoic acid derivatives 3 in high yields.
Amii
H
H
Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan.
Kishikawa
Y
Y
Kageyama
K
K
Uneyama
K
K
D000081:Acetamides / Q000138:chemical synthesis*; D000438:Alcohols / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D002384:Catalysis; D007454:Iodides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010165:Palladium
D000081:Acetamides; D000438:Alcohols; D000596:Amino Acids; D007454:Iodides; D010165:Palladium