Enantiodifferentiation by 1H and 13C NMR spectroscopy (dirhodium method) - Selectivity of oxygen functionalities

Edison Díaz Gómez, Sándor Antus, Renáta Ferenczi, Barbara Rys, Anna Stankiewicz, Helmut Duddecka

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Chiral carbonyl compounds can easily be enantiodifferentiated by the dirhodium method. The rhodium atoms reveal a remarkable selectivity in binding to oxygen atoms, which is of great advantage for discriminating chiral polyoxygenated natural products. Amides are the strongest ligands followed by ketones and esters; ethers and alcohols/phenols are even less effective. This sequence is rationalized by electronic charges at the oxygen atoms, as obtained from density functional calculations.

Original languageEnglish
Pages (from-to)339-343
Number of pages5
JournalNatural Product Communications
Volume3
Issue number3
Publication statusPublished - 2008

Fingerprint

nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
rhodium
Oxygen
oxygen
carbonyl compounds
Rhodium
Ethers
Phenols
amides
ketones
Biological Products
Ketones
Amides
phenols
electronics
ethers
Esters
alcohols
esters

Keywords

  • H and C NMR
  • Adduct formation
  • Chiral recognition
  • Density functional calculations
  • Dirhodium complexes

ASJC Scopus subject areas

  • Drug Discovery
  • Pharmacology
  • Complementary and alternative medicine
  • Plant Science

Cite this

Enantiodifferentiation by 1H and 13C NMR spectroscopy (dirhodium method) - Selectivity of oxygen functionalities. / Gómez, Edison Díaz; Antus, Sándor; Ferenczi, Renáta; Rys, Barbara; Stankiewicz, Anna; Duddecka, Helmut.

In: Natural Product Communications, Vol. 3, No. 3, 2008, p. 339-343.

Research output: Contribution to journalArticle

Gómez, Edison Díaz ; Antus, Sándor ; Ferenczi, Renáta ; Rys, Barbara ; Stankiewicz, Anna ; Duddecka, Helmut. / Enantiodifferentiation by 1H and 13C NMR spectroscopy (dirhodium method) - Selectivity of oxygen functionalities. In: Natural Product Communications. 2008 ; Vol. 3, No. 3. pp. 339-343.
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