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Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans.

Emily G BabcockMd Shafiqur RahmanJames E Taylor
Published in: Organic & biomolecular chemistry (2022)
Heterocyclisation of tert -butyldimethylsilyl (TBS) protected γ-hydroxy-α,β-unsaturated ketones catalysed by para -toluenesulfonic acid ( p -TSA) to form substituted furans is reported. The reaction proceeds under mild conditions at room temperature in methanol to give a range of furan products (21 examples, up to 98% yield). Mechanistic experiments suggest the reaction proceeds via in situ deprotection followed by catalytic dehydrative heterocyclisation.
Keyphrases
  • room temperature
  • molecular docking
  • ionic liquid