Enantioselective Synthesis of an Atropisomeric Diaryl Ether

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

Research output: Contribution to journalArticle

36 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.

LanguageEnglish
Pages3234-3237
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number17
Early online date17 Mar 2008
DOIs
Publication statusPublished - 14 Apr 2008
Externally publishedYes

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Ether
Ethers
sulfoxide
Sulfones
Thermodynamics
Oxidation

Cite this

Clayden, Jonathan ; Worrall, Christopher P. ; Moran, Wesley J. ; Helliwell, Madeleine. / Enantioselective Synthesis of an Atropisomeric Diaryl Ether. In: Angewandte Chemie - International Edition. 2008 ; Vol. 47, No. 17. pp. 3234-3237.
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Enantioselective Synthesis of an Atropisomeric Diaryl Ether. / Clayden, Jonathan; Worrall, Christopher P.; Moran, Wesley J.; Helliwell, Madeleine.

In: Angewandte Chemie - International Edition, Vol. 47, No. 17, 14.04.2008, p. 3234-3237.

Research output: Contribution to journalArticle

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