Alkynyltrifluoroborates as versatile tools in organic synthesis: a new route to spiroketals

Org Lett. 2004 Dec 23;6(26):4909-11. doi: 10.1021/ol047987k.

Abstract

[reaction: see text] A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl alpha-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroketal intermediate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Lithium / chemistry
  • Molecular Structure
  • Palladium / chemistry
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry

Substances

  • Boron Compounds
  • Spiro Compounds
  • Palladium
  • Lithium