Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis

Mark S. Betson; Ann Bracegirdle; Jonathan Clayden; Madeleine Helliwell; Andrew Lund; Mark Pickworth; Timothy J. Snape; Christopher P. Worrall

doi:10.1039/b614618j

Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis

Mark S. Betson, Ann Bracegirdle, Jonathan Clayden, Madeleine Helliwell, Andrew Lund, Mark Pickworth, Timothy J. Snape, Christopher P. Worrall

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

Abstract

The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N′-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95: 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond. © The Royal Society of Chemistry.

Original language	English
Pages (from-to)	754-756
Number of pages	2
Journal	Chemical Communications
Issue number	7
DOIs	https://doi.org/10.1039/b614618j
Publication status	Published - 2007

Keywords

ASYMMETRIC-SYNTHESIS
THERMODYNAMIC CONTROL
ATROPISOMERIC AMIDES
DYNAMIC RESOLUTION
AROMATIC AMIDES
STEREOCONTROL
STEREOCHEMISTRY
STEREODYNAMICS
COMMUNICATION
(-)-EPHEDRINE

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10.1039/b614618j

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@article{f01977dcd48b4b15bfe430e010919e5b,

title = "Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis",

abstract = "The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N′-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95: 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond. {\textcopyright} The Royal Society of Chemistry.",

keywords = "ASYMMETRIC-SYNTHESIS, THERMODYNAMIC CONTROL, ATROPISOMERIC AMIDES, DYNAMIC RESOLUTION, AROMATIC AMIDES, STEREOCONTROL, STEREOCHEMISTRY, STEREODYNAMICS, COMMUNICATION, (-)-EPHEDRINE",

author = "Betson, {Mark S.} and Ann Bracegirdle and Jonathan Clayden and Madeleine Helliwell and Andrew Lund and Mark Pickworth and Snape, {Timothy J.} and Worrall, {Christopher P.}",

note = "Betson, Mark S. Bracegirdle, Ann Clayden, Jonathan Helliwell, Madeleine Lund, Andrew Pickworth, Mark Snape, Timothy J. Worrall, Christopher P. 28 ROYAL SOC CHEMISTRY CAMBRIDGE 134YD",

year = "2007",

doi = "10.1039/b614618j",

language = "English",

pages = "754--756",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "7",

}

TY - JOUR

T1 - Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis

AU - Betson, Mark S.

AU - Bracegirdle, Ann

AU - Clayden, Jonathan

AU - Helliwell, Madeleine

AU - Lund, Andrew

AU - Pickworth, Mark

AU - Snape, Timothy J.

AU - Worrall, Christopher P.

N1 - Betson, Mark S. Bracegirdle, Ann Clayden, Jonathan Helliwell, Madeleine Lund, Andrew Pickworth, Mark Snape, Timothy J. Worrall, Christopher P. 28 ROYAL SOC CHEMISTRY CAMBRIDGE 134YD

PY - 2007

Y1 - 2007

N2 - The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N′-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95: 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond. © The Royal Society of Chemistry.

AB - The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N′-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95: 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond. © The Royal Society of Chemistry.

KW - ASYMMETRIC-SYNTHESIS

KW - THERMODYNAMIC CONTROL

KW - ATROPISOMERIC AMIDES

KW - DYNAMIC RESOLUTION

KW - AROMATIC AMIDES

KW - STEREOCONTROL

KW - STEREOCHEMISTRY

KW - STEREODYNAMICS

KW - COMMUNICATION

KW - (-)-EPHEDRINE

UR - https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/ccnxd97&sid=DataCite

UR - https://www.ccdc.cam.ac.uk/structures/search?id=doi:10.5517/ccnxd86&sid=DataCite

U2 - 10.1039/b614618j

DO - 10.1039/b614618j

M3 - Article

SP - 754

EP - 756

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 7

ER -

Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis

Abstract

Keywords

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CCDC 623110: Experimental Crystal Structure Determination

CCDC 623111: Experimental Crystal Structure Determination

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Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis

Abstract

Keywords

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Other files and links

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Datasets

CCDC 623110: Experimental Crystal Structure Determination

CCDC 623111: Experimental Crystal Structure Determination

Cite this