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


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Title: Oxidative C–C bond cleavage of N-alkoxycarbonylated cyclic amines by sodium nitrite in trifluoroacetic acid
Authors: Onomura, Osamu / Moriyama, Atsushi / Fukae, Kazuhiro / Yamamoto, Yutaka / Maki, Toshihide / Matsumura, Yoshihiro / Demizu, Yosuke
Issue Date: 17-Nov-2008
Publisher: Elsevier Ltd
Citation: Tetrahedron Letters, 49(47), pp.6728-6731; 2008
Abstract: 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.
Keywords: Carbon–carbon cleavage / Cyclic amines / Trifluoroacetic acid / Sodium nitrite / ω-Amino acid
URI: http://hdl.handle.net/10069/20093
ISSN: 00404039
DOI: 10.1016/j.tetlet.2008.09.067
Rights: Copyright © 2008 Elsevier Ltd All rights reserved.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/20093

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