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Synthesis of the 4‐Pyridine Analog of Kostanecki's Triketone. Determination of Constitution and Stereochemistry by 2D‐NMR Spectroscopy and X‐ray Structural Analysis
Author(s) -
Kessler Horst,
Mronga Siggi,
Kutscher Bernhard,
Müller Arndt,
Sheldrick William S.
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101228
Subject(s) - chemistry , benzaldehyde , stereochemistry , pyridine , single crystal , nuclear magnetic resonance spectroscopy , proton nmr , spectroscopy , two dimensional nuclear magnetic resonance spectroscopy , proton , crystallography , organic chemistry , catalysis , physics , quantum mechanics
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 3 J HH couplings. The stereochemistry at the non‐proton bearing C‐1 was established by through‐space connectivities from ROESY and semiquantitative analysis of 3 J CH from an inverse 2D‐NMR spectrum (HMBC). The NMR findings were confirmed by single crystal X‐ray diffraction.