Atropisomerism at C - S bonds: Asymmetric synthesis of diaryl sulfones by dynamic resolution under thermodynamic control

Jonathan Clayden*, James Senior, Madeleine Helliwell

*Corresponding author for this work

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

21 Citations (Scopus)

Abstract

A powerful conformational preference exhibited by a diaryl sulfone axis lying ortho to a sulfinyl substituent enabled the dynamic resolution of atropisomeric diaryl sulfones under thermodynamic control (see scheme; e.r.=enantiomeric ratio). These compounds are the first resolvable compounds exhibiting atropisomerism at C-S bonds.

Original languageEnglish
Pages (from-to)6270-6273
Number of pages4
JournalAngewandte Chemie - International Edition
Volume48
Issue number34
Early online date16 Jul 2009
DOIs
Publication statusPublished - 10 Aug 2009

Keywords

  • Atropisomerism
  • Dynamic resolution
  • Rotational barriers
  • Sulfones
  • Sulfoxides

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