Bidentate Lewis Acid Catalyzed Inverse-Electron-Demand Diels-Alder Reaction for the Selective Functionalization of Aldehydes - Forschungsportal der Justus-Liebig-Universität Gießen:

Journalartikel

Bidentate Lewis Acid Catalyzed Inverse-Electron-Demand Diels-Alder Reaction for the Selective Functionalization of Aldehydes

Autorenliste: Schweighauser, L; Bodoky, I; Kessler, SN; Häussinger, D; Wegner, HA

Jahr der Veröffentlichung: 2012

Seiten: 2195-2199

Zeitschrift: Synthesis: Journal of Synthetic Organic Chemistry

Bandnummer: 44

Heftnummer: 14

ISSN: 0039-7881

DOI Link: https://doi.org/10.1055/s-0031-1291127

Verlag: Thieme Publishing / Georg Thieme Verlag

Abstract:
The inverse-electron-demand Diels-Alder (IEDDA) reaction catalyzed by a bidentate Lewis acid was applied to enamines generated in situ from aldehydes. In general, a high functional group tolerance has been observed. Side reactions during the enamine forming step can limit the yield of the desired naphthalene. For citronellal as substrate, the initial intermediate after the catalyzed IEDDA reaction was trapped by an intramolecular Diels-Alder reaction to furnish a tricyclic compound. This scaffold represents the framework of natural products such as valerianoids A-C or the patchouli alcohol.

Autoren/Herausgeber

- Uni.-Prof. Dr. Hermann Andreas Wegner

Zitierstile

Harvard-Zitierstil: Schweighauser, L., Bodoky, I., Kessler, S., Häussinger, D. and Wegner, H. (2012) Bidentate Lewis Acid Catalyzed Inverse-Electron-Demand Diels-Alder Reaction for the Selective Functionalization of Aldehydes, Synthesis: Journal of Synthetic Organic Chemistry, 44(14), pp. 2195-2199. https://doi.org/10.1055/s-0031-1291127

APA-Zitierstil: Schweighauser, L., Bodoky, I., Kessler, S., Häussinger, D., & Wegner, H. (2012). Bidentate Lewis Acid Catalyzed Inverse-Electron-Demand Diels-Alder Reaction for the Selective Functionalization of Aldehydes. Synthesis: Journal of Synthetic Organic Chemistry. 44(14), 2195-2199. https://doi.org/10.1055/s-0031-1291127