Enantioselective synthesis of an atropisomeric diaryl ether

Jonathan Clayden*, Christopher P. Worrall, Wesley J. Moran, Madeleine Helliwell

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

39 Citations (Scopus)

Abstract

(Chemical Equation Presented) Twisted ethers: Introduction of a bulky alkylsulfinyl substituent ortho to the C-O axis of a diaryl ether imposes a powerful conformational preference (see scheme). The preference persists upon oxidation of the sulfoxide to a sulfone, leading to dynamic thermodynamic resolution of the atropisomeric ether. This is the first enantioselective synthesis of an atropisomeric diaryl ether not forming part of a macrocyclic ring.

Original languageEnglish
Pages (from-to)3234-3237
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number17
Early online date17 Mar 2008
DOIs
Publication statusPublished - 14 Apr 2008

Keywords

  • Atropisomerism
  • Conformation analysis
  • Diaryl ethers
  • Sulfur

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