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Synthesis 2012; 44(14): 2195-2199
DOI: 10.1055/s-0031-1291127
DOI: 10.1055/s-0031-1291127
special topic
Bidentate Lewis Acid Catalyzed Inverse-Electron-Demand Diels–Alder Reaction for the Selective Functionalization of Aldehydes
Weitere Informationen
Publikationsverlauf
Received: 03. April 2012
Accepted: 10. April 2012
Publikationsdatum:
25. Mai 2012 (online)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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