Base mediated deprotection strategies for trifluoroethyl (TFE) ethers, a new alcohol protecting group

Qingliang Yang, Jon T. Njardarson

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

A trifluoroethyl (TFE) ether is specifically introduced as a protecting group in organic chemistry. Its first strategic application and removal in the total synthesis of vinigrol is discussed. Two lithium base mediated deprotection strategies for its removal are presented in this Letter. In one deprotection approach, the trifluoroethyl ether is converted to a difluorovinyl ether and then catalytically cleaved using osmium tetraoxide, while in the second approach a difluorovinyl anion is formed and trapped with an electrophilic oxygen reagent (MoOPH) to form a labile difluoroacetate. To further aid the reader, a summary of approaches for forming trifluoroethyl ethers is included as well as a discussion of alternate deprotection strategies.

Original languageEnglish (US)
Pages (from-to)7080-7082
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number51
DOIs
StatePublished - Dec 18 2013

Keywords

  • Deprotection
  • Difluorovinyl
  • Dihydroxylation
  • Electrophilic oxygen
  • Trifluoroethyl ether

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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