Synthesis of the 4‐Pyridine Analog of Kostanecki's Triketone. Determination of Constitution and Stereochemistry by 2D‐NMR Spectroscopy and X‐ray Structural Analysis

Horst Kessler, Siggi onga, Bernhard Kutscher, Arndt Müller, William S. Sheldrick

Publikation: Beitrag in FachzeitschriftArtikelBegutachtung

14 Zitate (Scopus)

Abstract

4‐Acetylpyridine reacts stereoselectively with benzaldehyde under basic conditions to afford rac‐1. The constitution of 1 was determined by the long‐range connectivities revealed by the H, C‐COLOC spectrum. The relative stereochemistry of the chiral centers C‐2 to C‐6 was obtained from 3JHH couplings. The stereochemistry at the non‐proton bearing C‐1 was established by through‐space connectivities from ROESY and semiquantitative analysis of 3JCH from an inverse 2D‐NMR spectrum (HMBC). The NMR findings were confirmed by single crystal X‐ray diffraction.

OriginalspracheDeutsch
Seiten (von - bis)1337-1341
Seitenumfang5
FachzeitschriftLiebigs Annalen der Chemie
Jahrgang1991
Ausgabenummer12
DOIs
PublikationsstatusVeröffentlicht - 1991

Schlagwörter

  • Aldol reaction
  • Azachalcone
  • Inverse 2D‐NMR
  • Michael addition

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