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Synlett 2013; 24(10): 1238-1242
DOI: 10.1055/s-0033-1338946
DOI: 10.1055/s-0033-1338946
cluster
Gold(I)-Catalyzed Intramolecular [4+3]-Cycloaddition Reactions with Furan Propargyl Esters as the Substrates: Carbenoid vs. Stabilized Allyl Cation
Weitere Informationen
Publikationsverlauf
Received: 02. April 2013
Accepted after revision: 22. April 2013
Publikationsdatum:
28. Mai 2013 (online)


Abstract
The tricyclic ring system with an oxabicyclo[3.2.1]octadiene and a fused six-membered ring was produced efficiently using the readily available propargyl ester furan substrate in the presence of a Au(I) complex. The reaction involves a tandem 3,3-rearrangement of the propargyl ester followed by an intramolecular [4+3]-cycloaddition reaction. Both the primary ligand of the gold complex (N-heterocyclic carbene; NHC) and a neutral dynamic ligand (PhCN) are important for the success of the reaction.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett. Included are computational coordinates and experimental procedures as well as NMR spectra.
- Supporting Information