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

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

58 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 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

Research Groups and Themes

Organic & Biological

Keywords

Atropisomerism
Conformation analysis
Diaryl ethers
Sulfur

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title = "Enantioselective synthesis of an atropisomeric diaryl ether",

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.",

keywords = "Atropisomerism, Conformation analysis, Diaryl ethers, Sulfur",

author = "Jonathan Clayden and Worrall, \{Christopher P.\} and Moran, \{Wesley J.\} and Madeleine Helliwell",

year = "2008",

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day = "14",

doi = "10.1002/anie.200705660",

language = "English",

volume = "47",

pages = "3234--3237",

journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - Enantioselective synthesis of an atropisomeric diaryl ether

AU - Clayden, Jonathan

AU - Worrall, Christopher P.

AU - Moran, Wesley J.

AU - Helliwell, Madeleine

PY - 2008/4/14

Y1 - 2008/4/14

N2 - (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.

AB - (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.

KW - Atropisomerism

KW - Conformation analysis

KW - Diaryl ethers

KW - Sulfur

UR - https://www.scopus.com/pages/publications/45549091379

U2 - 10.1002/anie.200705660

DO - 10.1002/anie.200705660

M3 - Article (Academic Journal)

C2 - 18348136

AN - SCOPUS:45549091379

SN - 1433-7851

VL - 47

SP - 3234

EP - 3237

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 17

ER -

Enantioselective synthesis of an atropisomeric diaryl ether

Abstract

Research Groups and Themes

Keywords

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