Oxacycle Synthesis

  • Author: ChemistryViews.org
  • Published: 25 April 2014
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Journal of the American Chemical Society/American Chemical Society (ACS)
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Oxacycle Synthesis

Critical substructures in many bioactive molecules and natural products are ethers. They are typically synthesized through attack of a nucleophilic oxygen on an electrophilic carbon.

Rachel Willand-Charnley, Benjamin W. Puffer, and Patrick H. Dussault, University of Nebraska—Lincoln, USA, have demonstrated a new approach to synthesize spirocyclic ethers, aryl ethers, and various oxacycles including oxetanes.

They generated carbanions via chemoselective metal-heteroatom exchange or deprotonation. An intramolecular reaction of dialkyl peroxides with the carbanios leads to cyclic ethers. Applied in tandem with C−C bond formation, the strategy enables a one-step annelation to form oxaospirocycles.

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