TY - JOUR
T1 - Enantioselective synthesis of an atropisomeric diaryl ether
AU - Clayden, Jonathan
AU - Worrall, Christopher P.
AU - Moran, Wesley J.
AU - Helliwell, Madeleine
PY - 2008/4/14
Y1 - 2008/4/14
N2 - (Chemical Equation Presented) 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.
AB - (Chemical Equation Presented) 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.
KW - Atropisomerism
KW - Conformation analysis
KW - Diaryl ethers
KW - Sulfur
UR - http://www.scopus.com/inward/record.url?scp=45549091379&partnerID=8YFLogxK
U2 - 10.1002/anie.200705660
DO - 10.1002/anie.200705660
M3 - Article (Academic Journal)
C2 - 18348136
AN - SCOPUS:45549091379
SN - 1433-7851
VL - 47
SP - 3234
EP - 3237
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 17
ER -