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RESEARCH PRODUCT

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

Reijo SillanpääEnikő ForróMikko M. HänninenMárta PalkóGabriella BenedekEdit WéberFerenc FülöpFerenc Fülöp

subject

Inorganic ChemistryStereochemistryChemistryOrganic ChemistryPhysical and Theoretical ChemistryEnantiomerSpectroscopyTwo-dimensional nuclear magnetic resonance spectroscopyCatalysis

description

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 OsO4-catalyzed 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.

yearjournalcountryeditionlanguage
2010-04-01Tetrahedron: Asymmetry
https://doi.org/10.1016/j.tetasy.2010.05.003