103898-09-5Relevant articles and documents
Chemical Conversion of Cyclic α-Amino Acids to α-Aminodicarboxylic Acids by Improved Ruthenium Tetroxide Oxidation
Yoshifuji, Shigeyuki,Tanaka, Ken-ichi,Kawai, Tomoyuki,Nitta, Yoshihiro
, p. 5515 - 5521 (2007/10/02)
The ruthenium tetroxide (RuO4) oxidation of N-acylated L-proline esters, prepared from L-proline, was carried out under two-phase conditions to afford good yields of the corresponding lactams with no appreciable racemization, and the products were hydrolyzed in aqueous hydrochloric acid to L-glutamic acid.Similar transformation starting with racemic 2-piperidinecaboxylic acid and 2-azetidinecarboxylic acid gave 2-aminoadipic acid and aspartic acid, respectively.A novel chemical converion of cyclic α-amino acids into α-aminodicarboxylic acids has been accomplished.A new solvent system, ethyl acetate-water, was developed for this two-phase oxidation.It was found to be very useful in reducing the necessary reaction time.Keywords --- oxidation; regioselectivity; lactam synthesis; ruthenium tetroxide; cyclic α-amino acid; α-aminodicarboxylic acid; L-proline; L-glutamic acid; two-phase method; ethyl acetate-water system
