Efficient synthesis of 3,4- and 4,5-dihydroxy-2-amino-cyclohexanecarboxylic acid enantiomers

Gabriella Benedek, Márta Palkó, Edit Wéber, T. Martinek, E. Forró, F. Fülöp

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

An efficient method for the synthesis of (1S,2R,4R,5S)- and (1R,2R,4R,5S)-2-amino-4,5-dihydroxycyclohexanecarboxylic acids (-)-6 and (-)-9 and (1R,2R,3S,4R)- and (1S,2R,3S,4R)-2-amino-3,4-dihydroxycyclohexanecarboxylic acids (-)-15 and (-)-18 was developed by using the OsO4-catalyzed oxidation of Boc-protected (1S,2R)-2-aminocyclohex-4-enecarboxylic acid (+)-2 and (1R,2S)-2-aminocyclohex-3-enecarboxylic acid (+)-11. Good yields were obtained. The stereochemistry of the synthesized compounds was proven by NMR spectroscopy.

Original languageEnglish
Pages (from-to)2220-2225
Number of pages6
JournalTetrahedron Asymmetry
Volume20
Issue number19
DOIs
Publication statusPublished - Oct 6 2009

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Enantiomers
enantiomers
amino acids
Amino acids
acids
Acids
synthesis
Stereochemistry
stereochemistry
Nuclear magnetic resonance spectroscopy
Oxidation
nuclear magnetic resonance
oxidation
cyclohexanecarboxylic acid
spectroscopy

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Efficient synthesis of 3,4- and 4,5-dihydroxy-2-amino-cyclohexanecarboxylic acid enantiomers. / Benedek, Gabriella; Palkó, Márta; Wéber, Edit; Martinek, T.; Forró, E.; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 20, No. 19, 06.10.2009, p. 2220-2225.

Research output: Contribution to journalArticle

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AU - Forró, E.

AU - Fülöp, F.

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