US EPA

7452450 

Journal Article 

Ruthenium Tetroxide Oxidation of N-Acyl Amines and Related Compounds 

Kaname, M; Yoshifuji, S; Sashida, H 

2011 

1 

Yuki Gosei Kagaku Kyokaishi
ISSN: 0037-9980 

69 

10 

1109-1121 

Japanese 

10.5059/yukigoseikyokaishi.69.1109 

WOS:000296036300004 

The basic utility and application of ruthenium tetroxide (RuO4) oxidation of N-acyl amines and their related compounds including optically active substrates are described. The oxidation of acyclic and cyclic iV-acyl amines proceeded smoothly at room temperature by active RuO4, which was generated in situ from a catalytic amount of ruthenium dioxide (RuO 2.xH2O) and an excess of 10% aqueous sodium metaperiodate (NaIO4) in a double layer system of ethyl acetate-water to afford the corresponding imides in good to excellent yields. Cyclic ene-carbamates were oxidized at their carbon-carbon double bond to produce ω-(N-formylamino) carboxylic acids as the major products. The conventional double layer system of the reaction medium was changed to a single layer aqueous system containing terf-butanol, in which oxidation directly cleaved the endo-cycXic C-N bond to give ω-amino acids as the sole open-ring products. The syntheses of baclofen, lycoperdic acid, optically active pyrrolidine-3-phosphonic acids and L-carnitine were accomplished using RuO4 oxidation as the key step. 

ruthenium tetroxide oxidation; N-acyl amine; N-acyl amide; N-acyl lactam; alpha-aminodicarboxylic acid; cyclic ene-carbamate; endo-cyclic carbon-carbon double bond cleavage; lycoperdic acid; baclofen; carnitine