Atropisomerism at C - S bonds: Asymmetric synthesis of diaryl sulfones by dynamic resolution under thermodynamic control

Jonathan Clayden; James Senior; Madeleine Helliwell

doi:10.1002/anie.200901718

Atropisomerism at C - S bonds: Asymmetric synthesis of diaryl sulfones by dynamic resolution under thermodynamic control

Jonathan Clayden^*, James Senior, Madeleine Helliwell

^*Corresponding author for this work

School of Chemistry

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

39 Citations (Scopus)

Abstract

A powerful conformational preference exhibited by a diaryl sulfone axis lying ortho to a sulfinyl substituent enabled the dynamic resolution of atropisomeric diaryl sulfones under thermodynamic control (see scheme; e.r.=enantiomeric ratio). These compounds are the first resolvable compounds exhibiting atropisomerism at C-S bonds.

Original language	English
Pages (from-to)	6270-6273
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	34
Early online date	16 Jul 2009
DOIs	https://doi.org/10.1002/anie.200901718
Publication status	Published - 10 Aug 2009

Keywords

Atropisomerism
Dynamic resolution
Rotational barriers
Sulfones
Sulfoxides

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title = "Atropisomerism at C - S bonds: Asymmetric synthesis of diaryl sulfones by dynamic resolution under thermodynamic control",

abstract = "A powerful conformational preference exhibited by a diaryl sulfone axis lying ortho to a sulfinyl substituent enabled the dynamic resolution of atropisomeric diaryl sulfones under thermodynamic control (see scheme; e.r.=enantiomeric ratio). These compounds are the first resolvable compounds exhibiting atropisomerism at C-S bonds.",

keywords = "Atropisomerism, Dynamic resolution, Rotational barriers, Sulfones, Sulfoxides",

author = "Jonathan Clayden and James Senior and Madeleine Helliwell",

year = "2009",

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T1 - Atropisomerism at C - S bonds

T2 - Asymmetric synthesis of diaryl sulfones by dynamic resolution under thermodynamic control

AU - Clayden, Jonathan

AU - Senior, James

AU - Helliwell, Madeleine

PY - 2009/8/10

Y1 - 2009/8/10

N2 - A powerful conformational preference exhibited by a diaryl sulfone axis lying ortho to a sulfinyl substituent enabled the dynamic resolution of atropisomeric diaryl sulfones under thermodynamic control (see scheme; e.r.=enantiomeric ratio). These compounds are the first resolvable compounds exhibiting atropisomerism at C-S bonds.

AB - A powerful conformational preference exhibited by a diaryl sulfone axis lying ortho to a sulfinyl substituent enabled the dynamic resolution of atropisomeric diaryl sulfones under thermodynamic control (see scheme; e.r.=enantiomeric ratio). These compounds are the first resolvable compounds exhibiting atropisomerism at C-S bonds.

KW - Atropisomerism

KW - Dynamic resolution

KW - Rotational barriers

KW - Sulfones

KW - Sulfoxides

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U2 - 10.1002/anie.200901718

DO - 10.1002/anie.200901718

M3 - Article (Academic Journal)

C2 - 19610006

AN - SCOPUS:70349933112

SN - 1433-7851

VL - 48

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EP - 6273

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 34

ER -

Atropisomerism at C - S bonds: Asymmetric synthesis of diaryl sulfones by dynamic resolution under thermodynamic control

Abstract

Keywords

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