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Atropisomerism at CS Bonds: Asymmetric Synthesis of Diaryl Sulfones by Dynamic Resolution Under Thermodynamic Control
Author(s) -
Clayden Jonathan,
Senior James,
Helliwell Madeleine
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200901718
Subject(s) - atropisomer , enantiomer , substituent , chemistry , sulfone , preference , resolution (logic) , stereochemistry , computer science , combinatorial chemistry , organic chemistry , mathematics , artificial intelligence , statistics
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 CS bonds.