Enantioselective Synthesis of an Atropisomeric Diaryl Ether

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

doi:10.1002/anie.200705660

Enantioselective Synthesis of an Atropisomeric Diaryl Ether

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

Research output: Contribution to journal › Article › peer-review

56 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 language	English
Pages (from-to)	3234-3237
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	17
Early online date	17 Mar 2008
DOIs	https://doi.org/10.1002/anie.200705660
Publication status	Published - 14 Apr 2008
Externally published	Yes

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10.1002/anie.200705660

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AU - Worrall, Christopher P.

AU - Moran, Wesley J.

AU - Helliwell, Madeleine

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AB - 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.

KW - Atropisomerism

KW - Conformation analysis

KW - Diaryl ethers

KW - Sulfur

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ER -

Enantioselective Synthesis of an Atropisomeric Diaryl Ether

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