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

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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.

Original languageGerman
Pages (from-to)1337-1341
Number of pages5
JournalLiebigs Annalen der Chemie
Volume1991
Issue number12
DOIs
StatePublished - 1991

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