Oxidative C-C bond cleavage of N-alkoxycarbonylated cyclic amines by sodium nitrite in trifluoroacetic acid

Oxidative carbon-carbon bond cleavage of N-alkoxycarbonylated cyclic amines was accomplished by NaNO2 in TFA to afford ω-amino carboxylic acid in high yield. Optically active 3-hydroxypiperidine derivatives and 3-pipecolinate were converted to enantiomerically pure (R)-4-amino-3-hydroxybutanoic acid (GABOB) and (S)-2-pyrrolidone-4-carboxylate, respectively.