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Ynol Ethers as Ketene Equivalents in Rhodium-Catalyzed Intermolecular [5 + 2] Cycloaddition Reactions.

Paul A WenderChristian EbnerBrandon D FennellFuyuhiko InagakiBirte Schröder
Published in: Organic letters (2018)
The previously unexplored metal-catalyzed [5 + 2] cycloadditions of vinylcyclopropanes (VCPs) and electron-rich alkynes (ynol ethers) have been found to provide a highly efficient, direct route to dioxygenated seven-membered rings, a common feature of numerous natural and non-natural targets and building blocks for synthesis. The reactions proceed in high yield at room temperature and tolerate a broad range of functionalities. Substituted VCPs were found to react with high regioselectivity.
Keyphrases
  • room temperature
  • highly efficient
  • ionic liquid
  • machine learning
  • molecular docking
  • deep learning
  • molecular dynamics simulations