論文

2019年1月1日

Highly Chemoselective gem-Difluoropropargylation of Aliphatic Alcohols

Chemistry - A European Journal
  • Toshitaka Okamura
  • ,
  • Syusuke Egoshi
  • ,
  • Kosuke Dodo
  • ,
  • Mikiko Sodeoka
  • ,
  • Yoshiharu Iwabuchi
  • ,
  • Naoki Kanoh

DOI
10.1002/chem.201904366

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Despite the potential of α-fluoroethers in medicinal chemistry, their synthetic methods, especially etherification of aliphatic alcohols, have been limited. Herein, we developed two- and three-step gem-difluoropropargylation of aliphatic alcohols including amino acid derivatives and naturally occurring bioactive molecules. Highly chemoselective etherification proceeded by using the gem-difluoropropargyl bromide dicobalt complex in the presence of silver triflate and triethylamine. Decomplexation of dicobalt complexes was achieved by using cerium ammonium nitrate or N,N,N′-trimethylethylenediamine. The thus obtained gem-difluoropropargyl ethers were converted to various α-difluoroethers which are expected to be useful for medicinal chemistry.

リンク情報
DOI
https://doi.org/10.1002/chem.201904366
URL
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85074994424&origin=inward

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