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 m...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2009-01, Vol.7 (19), p.3991-3999
Main Authors: García-Egido, Eduardo, Paz, Jairo, Iglesias, Beatriz, Muñoz, Luis
Format: Article
Language:English
Subjects:
Amines - chemistry
Amino Alcohols - chemistry
Atmospheric Pressure
Bromobenzenes - chemical synthesis
Bromobenzenes - chemistry
Carbon Dioxide - chemistry
Formamides - chemical synthesis
Formamides - chemistry
Nitriles - chemical synthesis
Nitriles - chemistry
Organophosphonates - chemistry
Oxazolidinones - chemistry
Temperature
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/b912043b