Generation of cycloheptynes and cyclooctynes via a sulfoxide-magnesium exchange reaction of readily synthesized 2-sulfinylcycloalkenyl triflates

Chem Commun (Camb). 2015 May 25;51(42):8745-8. doi: 10.1039/c5cc01784j.

Abstract

Cycloheptynes and cyclooctynes were efficiently generated via a sulfoxide-magnesium exchange reaction of readily synthesized 2-sulfinylcycloalkenyl triflates. Cycloadditions between various ynophiles and the cycloalkynes generated by this method proceeded efficiently, providing an easy method to prepare a wide range of heterocycles fused with seven- or eight-membered carbocycles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Cycloparaffins / chemical synthesis*
  • Cycloparaffins / chemistry
  • Magnesium / chemistry*
  • Mesylates / chemical synthesis*
  • Mesylates / chemistry
  • Molecular Structure
  • Sulfoxides / chemical synthesis*
  • Sulfoxides / chemistry*

Substances

  • Cycloparaffins
  • Mesylates
  • Sulfoxides
  • Magnesium