An efficient approach to the synthesis of 3-vinylidene tetrahydropyrans via Prins-type cyclization

  • Dziedzic M
  • Lipner G
  • Furman B
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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. © 2005 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • Prins cyclization
  • Propargylsilanes
  • Tetrahydropyrans

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Authors

  • Magdalena Dziedzic

  • Grzegorz Lipner

  • Bartłomiej Furman

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