新合成試薬ジエチルリン酸シアニド(DEPC)

概要

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Synthetic utilities of diethyl phosphorocyanidate (DEPC) are reviewed. Interaction of DEPC with carboxylic acids in the presence of triethylamine produces carboxyl-activated compounds such as acyl phosphates and/or acyl cyanides, which can easily couple with amines, thiols, alcohols, and active methylene compounds to give amides and peptides, thiol esters, carboxylic esters, and C-acylated products, respectively. Penicillin sulfoxides give 3-cephem as well as 3-methylenecepham derivatives by ring expansion with DEPC. DEPC can be also used as a cyanation reagent for C<SUB>1</SUB>-unit introduction to enamines and carbonyl compounds, the latter of which gives α-amino nitriles on treatment with DEPC and amines. Physiological properties of DEPC are also discussed.
社団法人有機合成化学協会の論文