Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans

Org Biomol Chem. 2022 Dec 21;21(1):163-168. doi: 10.1039/d2ob01828d.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids
  • Catalysis
  • Furans*
  • Ketones
  • Methanol*

Substances

  • Furans
  • Methanol
  • Ketones
  • Acids