Improved synthesis of trans-4-alkylcyclohexane carboxylic acids

[Display omitted] Several stereomerically pure amino acid derivatives containing the N-terminal trans-4-alkylcyclohexanoyl fragment were obtained. Hydrogenation of 4-alkylbenzoic acids in the presence of a special Ru–Ni/C catalytic system and isomerization of the resulting mixture of trans- and cis-...

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Bibliographic Details
Published in:Tetrahedron letters 2004-08, Vol.45 (35), p.6669-6672
Main Authors: Bazurin, Alexey A., Krasnikov, Sergey V., Obuchova, Tatiana A., Danilova, Angelina S., Balakin, Konstantin V.
Format: Article
Language:English
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Summary:[Display omitted] Several stereomerically pure amino acid derivatives containing the N-terminal trans-4-alkylcyclohexanoyl fragment were obtained. Hydrogenation of 4-alkylbenzoic acids in the presence of a special Ru–Ni/C catalytic system and isomerization of the resulting mixture of trans- and cis-isomers of 4-alkylcyclohexanecarboxylic acids were used as the key steps. The stereomeric configuration of all compounds was confirmed by 1H NMR spectroscopy. The compounds obtained possess a broad biological activity potential and are useful intermediates in the synthesis of stereomerically pure modified peptides.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.06.117