Synthesis of mono- and dihydroxy-substituted 2-aminocyclooctanecarboxylic acid enantiomers

Márta Palkó, Gabriella Benedek, E. Forró, Edit Wéber, Mikko Hänninen, Reijo Sillanpää, F. Fülöp

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

(1R,2S,6R)-2-Amino-6-hydroxycyclooctanecarboxylic acid (-)-10 was synthesized from (1R,2S)-2-aminocyclooct-5-enecarboxylic acid (+)-2 via an iodolactone intermediate, while (1R,2S,3R,4S)-2-amino-5,6- dihydroxycyclooctanecarboxylic acid (-)-12 was prepared by using the OsO 4catalysed oxidation of Boc-protected amino ester (-)-5. The stereochemistry and relative configurations of the synthesized compounds were determined by 1D and 2D NMR spectroscopy (based on 2D NOE cross-peaks and 3J(H,H) coupling constants) and X-ray crystallography.

Original languageEnglish
Pages (from-to)957-961
Number of pages5
JournalTetrahedron Asymmetry
Volume21
Issue number8
DOIs
Publication statusPublished - 2010

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Enantiomers
enantiomers
acids
Acids
synthesis
Stereochemistry
X ray crystallography
stereochemistry
Nuclear magnetic resonance spectroscopy
crystallography
esters
Esters
Oxidation
nuclear magnetic resonance
oxidation
configurations
spectroscopy
x rays

ASJC Scopus subject areas

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

Cite this

Synthesis of mono- and dihydroxy-substituted 2-aminocyclooctanecarboxylic acid enantiomers. / Palkó, Márta; Benedek, Gabriella; Forró, E.; Wéber, Edit; Hänninen, Mikko; Sillanpää, Reijo; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 21, No. 8, 2010, p. 957-961.

Research output: Contribution to journalArticle

Palkó, Márta ; Benedek, Gabriella ; Forró, E. ; Wéber, Edit ; Hänninen, Mikko ; Sillanpää, Reijo ; Fülöp, F. / Synthesis of mono- and dihydroxy-substituted 2-aminocyclooctanecarboxylic acid enantiomers. In: Tetrahedron Asymmetry. 2010 ; Vol. 21, No. 8. pp. 957-961.
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AU - Wéber, Edit

AU - Hänninen, Mikko

AU - Sillanpää, Reijo

AU - Fülöp, F.

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AB - (1R,2S,6R)-2-Amino-6-hydroxycyclooctanecarboxylic acid (-)-10 was synthesized from (1R,2S)-2-aminocyclooct-5-enecarboxylic acid (+)-2 via an iodolactone intermediate, while (1R,2S,3R,4S)-2-amino-5,6- dihydroxycyclooctanecarboxylic acid (-)-12 was prepared by using the OsO 4catalysed oxidation of Boc-protected amino ester (-)-5. The stereochemistry and relative configurations of the synthesized compounds were determined by 1D and 2D NMR spectroscopy (based on 2D NOE cross-peaks and 3J(H,H) coupling constants) and X-ray crystallography.

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