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An efficient approach to the synthesis of 3-vinylidene tetrahydropyrans via Prins-type cyclization
Authors:Magdalena Dziedzic  Bart?omiej Furman
Affiliation:Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Abstract:
Lewis acid-catalyzed intramolecular reactions of oxocarbenium ions with propargylsilanes are described. The results obtained indicate that trimethylsilyl trifluoromethanesulfonate (TMSOTf) efficiently catalyses cyclization leading to the corresponding 3-vinylidene tetrahydropyrans in high yield as single isomers.
Keywords:Propargylsilanes   Tetrahydropyrans   Prins cyclization
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