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- W2513367789 abstract "Abstract Gold‐catalyzed cyclization of various furan‐ynes with a propargyl carbonate or ester moiety results in the formation of a series of polycyclic aromatic ring systems. The reactions can be rationalized through a tandem gold‐catalyzed 3,3‐rearrangement of the propargyl carboxylate moiety in furan‐yne substrates to form an allenic intermediate, which is followed by an intramolecular Diels–Alder reaction of furan and subsequent ring‐opening of the oxa‐bridged cycloadduct. It was found that the steric and electronic properties of phosphine ligands on the gold catalyst had a significant impact on the reaction outcome. In the case of 1,5‐furan‐yne, the cleavage of the oxa‐bridge in the cycloadduct with concomitant 1,2‐migration of the R 1 group occurs to furnish anthracen‐1(2 H )‐ones bearing a quaternary carbon center. For 1,4‐furan‐yne, a facile aromatization of the cycloadduct takes place to give 9‐oxygenated anthracene derivatives." @default.
- W2513367789 created "2016-09-16" @default.
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- W2513367789 date "2016-08-18" @default.
- W2513367789 modified "2023-10-14" @default.
- W2513367789 title "Gold-Catalyzed Cyclization of Furan-Ynes bearing a Propargyl Carbonate Group: Intramolecular Diels-Alder Reaction with In Situ Generated Allenes" @default.
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- W2513367789 doi "https://doi.org/10.1002/chem.201603055" @default.
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