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Enantioselective Synthesis of an Atropisomeric Diaryl Ether
Author(s) -
Clayden Jonathan,
Worrall Christopher P.,
Moran Wesley J.,
Helliwell Madeleine
Publication year - 2008
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.200705660
Subject(s) - enantioselective synthesis , ether , sulfone , substituent , sulfoxide , chemistry , atropisomer , ring (chemistry) , organic chemistry , catalysis
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.
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