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

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. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

Original language	English
Pages (from-to)	3234-3237
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	17
DOIs	https://doi.org/10.1002/anie.200705660
Publication status	Published - 14 Apr 2008

Keywords

Atropisomerism
Conformation analysis
Diaryl ethers
Sulfur

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10.1002/anie.200705660

http://www3.interscience.wiley.com/cgi-bin/fulltext/117935107/PDFSTART

CCDC 669806: Experimental Crystal Structure Determination
Clayden, J. (Contributor), Worrall, C. P. (Contributor), Moran, W. J. (Contributor) & Helliwell, M. (Contributor), Cambridge Crystallographic Data Centre, 2007
DOI: 10.5517/ccqgzns, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccqgzns&sid=DataCite
Dataset
CCDC 669807: Experimental Crystal Structure Determination
Clayden, J. (Contributor), Worrall, C. P. (Contributor), Moran, W. J. (Contributor) & Helliwell, M. (Contributor), Cambridge Crystallographic Data Centre, 2007
DOI: 10.5517/ccqgzpt, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccqgzpt&sid=DataCite
Dataset
CCDC 669805: Experimental Crystal Structure Determination
Clayden, J. (Contributor), Worrall, C. P. (Contributor), Moran, W. J. (Contributor) & Helliwell, M. (Contributor), Cambridge Crystallographic Data Centre, 2007
DOI: 10.5517/ccqgzmr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccqgzmr&sid=DataCite
Dataset

Cite this

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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. {\textcopyright} 2008 Wiley-VCH Verlag GmbH & Co. KGaA.",

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

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

year = "2008",

month = apr,

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. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

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. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

KW - Atropisomerism

KW - Conformation analysis

KW - Diaryl ethers

KW - Sulfur

U2 - 10.1002/anie.200705660

DO - 10.1002/anie.200705660

M3 - Article

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

Keywords

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Datasets

CCDC 669806: Experimental Crystal Structure Determination

CCDC 669807: Experimental Crystal Structure Determination

CCDC 669805: Experimental Crystal Structure Determination

Cite this