An efficient transformation of cyclic ene-carbamates into ω-(N-formylamino)carboxylic acids by ruthenium tetroxide oxidation

Abstract

The ruthenium tetroxide (RuO4) oxidation of cyclic ene-carbamates resulted in the endo-cyclic carbon-carbon double bond cleavage to afford the corresponding ω-(N-formylamino)carboxylic acids in good yields. Substituted cyclic ene-carbamates derived from (3R)-3-hydroxypiperidine hydrochloride were converted into the N-Boc 4-aminobutyric acids by utilization of the RuO4 oxidation as the key step, which were further transformed into (3R)-4-amino-3-hydroxybutyric acid, an important key intermediate for the synthesis of L-carnitine. © 2008 Pharmaceutical Society of Japan.