Synthesis of cyanoformamides from primary amines and carbon dioxide under mild conditions. Synthesis of ceratinamine.
Treatment of primary amines with tetramethylphenylguanidine (PhTMG) and a cyanophosphonate at -10 degrees Celsius under an atmosphere of carbon dioxide provides cyanoformamides in very high to excellent yields. The reaction proceeds efficiently within a short time. By-products were not detected in most runs and epimerization was not found when optically pure alpha-aminoesters were used as substrates. As an example, the reaction was applied to the synthesis of the marine natural product ceratinamine.
García-Egido
Eduardo
E
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain.
Paz
Jairo
J
Iglesias
Beatriz
B
Muñoz
Luis
L
D000588:Amines / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry; D001274:Atmospheric Pressure; D001969:Bromobenzenes / Q000138:chemical synthesis* / Q000737:chemistry; D002245:Carbon Dioxide / Q000737:chemistry*; D005559:Formamides / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry; D023303:Oxazolidinones / Q000737:chemistry; D013696:Temperature
D000588:Amines; D000605:Amino Alcohols; D001969:Bromobenzenes; D005559:Formamides; D009570:Nitriles; D063065:Organophosphonates; D023303:Oxazolidinones; C545831:ceratinamine; D002245:Carbon Dioxide