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Pentannulation Reaction by Tandem Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Nazarov Cyclization of Enynyl Vinyl Ethers. 2018
Antonia Rinaldi, and
Martina Petrović, and
Stefano Magnolfi, and
Dina Scarpi, and
Ernesto G Occhiato
Department of Chemistry "U. Schiff" , University of Florence , Via della Lastruccia 13 , 50019 , Sesto Fiorentino (FI) , Florence , Italy.
The tandem gold(I)-catalyzed propargyl Claisen rearrangement/Nazarov cyclization of propargyl vinyl ether derivatives, followed by in situ reduction of the resulting carbonyl group, provides functionalized cyclopentadienes fused with various N-hetero- and carbacycles, including indoles, in good to excellent yields. The reaction occurs with high regioselectivity, with the position of the double bonds in the five-membered ring depending on the type of (hetero)cycle bearing the propargylic moiety and the side chain on the latter.
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