Enantioselective Synthesis of an Atropisomeric Diaryl Ether

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

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

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
Externally publishedYes

Fingerprint Dive into the research topics of 'Enantioselective Synthesis of an Atropisomeric Diaryl Ether'. Together they form a unique fingerprint.

  • Cite this