Synthesis of cyanoformamides from primary amines and carbon dioxide under mild conditions. Synthesis of ceratinamine†
Eduardo García-Egido,Jairo Paz,Beatriz Iglesias,Luis Muñoz
Organic & Biomolecular Chemistry Pub Date : 07/23/2009 00:00:00 , DOI:10.1039/B912043B
Abstract

Treatment of primary amines with tetramethylphenylguanidine (PhTMG) and a cyanophosphonate at −10 °C 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 α-aminoesters were used as substrates. As an example, the reaction was applied to the synthesis of the marine natural product ceratinamine.

Graphical abstract: Synthesis of cyanoformamides from primary amines and carbon dioxide under mild conditions. Synthesis of ceratinamine