(Cyanomethylene)phosphoranes as Novel Carbonyl 1,1-Dipole Synthons: An Efficient Synthesis of α-Keto Acids, Esters, and Amides

Article abstract of DOI:10.1021/jo00095a005

Carboxylic acids react with (cyanomethylene)triphenylphosphorane in the presence of EDCI to form cyano keto phosphoranes.The resulting ylides may then be oxidatively cleaved with ozone to form α,β-diketonitriles.These highly electrophilic products may then be converted in situ to α-keto acids, esters, and amides.