Summary
Analogous to the recently described synthesis of Reissert epoxides the treatment of 1-acyl-2-alkyl-1,2-dihydroquinolines withm-chloroperoxybenzoic acid gave diasteromeric pure epoxides which are stable in crystalline state, but reactive in solution versus nucleophiles. Acting as useful intermediates to stereocontrolled functionalized 1,2,3,4-tetrahydroquinolines an X-ray analysis was performed to confirm the relative stereochemistry of the epoxides.
Zusammenfassung
Analog zu der kürzlich beschriebenen Synthese von Reissert-Epoxiden liefern 1-Acyl-2-alkyl-1,2-dihydrochinoline bei Behandlung mitm-Chlorperbenzoesäure diastereomerenreine Epoxide, die sich als Festsubstanzen außerordentlich stabil, in Lösung aber reaktiv gegenüber Nucleophilen erweisen. Da sie wertvolle Ausgangsverbindungen zu 1,2,3,4-substituierten Tetrahydrochinolinen mit definierter relativer Konfiguration darstellen, wurde die Stereochemie der Epoxide mittels Röntgenstrukturanalyse abgesichert.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Kratzel M., Hiessböck R. (1993) Monatsh. Chem., in press
Günther H. (1983) NMR-Spektroskopie. Thieme, Stuttgart, p. 110.
Kratzel M., Hiessböck R., Synth. Commun., in press
Goldstein S. W., Dambek P. J. (1989) Synthesis: 221
Buckle D. R., Eggleston D. S., Houge-Frydrych C. S. V., Pinto I. L., Readshaw S. A., Smith D. G., Webster R. A. B. (1991) J. Chem. Soc. Perkin Trans.I: 2763
Kratzel M., Hiessböck R., Heterocycles, accepted
Main P. (1978) MULTAN 78, System of Computer Programs for Automatic Solution of Crystal Structures from X-ray Diffraction Data. University of York, Great Britain
Sheldrick G. M. (1976) SHELX 76, Program for Crystal Structure Determination. University of Cambridge, Great Britain
Kratzel M. (1988) CHEM-CAD and ALCHPLOT, PC-Programs for 2D-Plots of Chemical Structures and 3D-Plots from Crystal Structures and ALCHEMY Data. Universität Wien, Österreich
Additional material to the structure determination can be ordered from Fachinformationszentrum Energie-Physik-Mathematik, D-76344 Eggenstein-Leopoldshafen 2, Federal Republic of Germany, referring to the deposition no. CSD-57794, the names of the authors and the citation of the paper
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kratzel, M., Hiessböck, R. & Völlenkle, H. Synthesis and stereochemistry of 1-acyl-2-alkyl-1,2,3,4-tetrahydroquinoline-3,4-epoxides. Monatsh Chem 125, 963–969 (1994). https://doi.org/10.1007/BF00812711
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00812711