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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

✍ Scribed by Kessler, Horst ;Mronga, Siggi ;Kutscher, Bernhard ;Müller, Arndt ;Sheldrick, William S.

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
484 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

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 ^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.

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