Journal article
Authors list: Schweighauser, L; Bodoky, I; Kessler, SN; Häussinger, D; Wegner, HA
Publication year: 2012
Pages: 2195-2199
Journal: Synthesis: Journal of Synthetic Organic Chemistry
Volume number: 44
Issue number: 14
ISSN: 0039-7881
DOI Link: https://doi.org/10.1055/s-0031-1291127
Publisher: 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.
Citation Styles
Harvard Citation style: 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 Citation style: 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
