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

✍ Scribed by Osamu Onomura; Atsushi Moriyama; Kazuhiro Fukae; Yutaka Yamamoto; Toshihide Maki; Yoshihiro Matsumura; Yosuke Demizu

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 180 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.09.067

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✦ Synopsis

Oxidative carbon-carbon bond cleavage of N-alkoxycarbonylated cyclic amines was accomplished by NaNO 2 in TFA to afford x-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.

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