Atropisomerism at C----S Bonds: Asymmetric Synthesis of Diaryl Sulfones by Dynamic Resolution Under Thermodynamic Control

Atropisomerism at C----S Bonds: Asymmetric Synthesis of Diaryl Sulfones by Dynamic Resolution Under Thermodynamic Control

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 exhibiti...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-08, Vol.48 (34), p.6270-6273
Hauptverfasser: Clayden, Jonathan, Senior, James, Helliwell, Madeleine
Format: Artikel
Sprache:eng
Schlagworte:
atropisomerism
Crystallography, X-Ray
dynamic resolution
Isomerism
Molecular Conformation
rotational barriers
sulfones
Sulfones - chemical synthesis
Sulfones - chemistry
sulfoxides
Sulfoxides - chemistry
Thermodynamics
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200901718