Three groups good, four groups bad?: Atropisomerism in ortho-substituted diaryl ethers

被引：64
作者：
Betson, Mark S.
Clayden, Jonathan
Worrall, Christopher R.
Peace, Simon
机构：
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[2] GlaxoSmithKline Med Res Ctr, Stevenage SG1 2NY, Herts, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 35期
关键词：
atropisomerism; diaryl ethers; NMR spectroscopy; rotational barriers; stereochemistry;
D O I：
10.1002/anie.200601866
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Bring on the substitute: Even outside of macrocyclic structures, such as vancomycin, appropriate substitution can give rise to atropisomerism in diaryl ethers. Stereochemical stability about the Ar-OAr axis at room temperature or above is possible when neither of the rings is symmetrically substituted and when at least one ring carries an ortho tert-butyl group or equivalent. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
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收藏
页码：5803 / 5807
页数：5
相关论文
共 46 条
[1]   The stereochemistry of diphenyls and analogous compounds [J].
Adams, R ;
Yuan, HC .
CHEMICAL REVIEWS, 1933, 12 (02) :261-338
[2]   Barriers to rotation about the chiral axis of tertiary aromatic amides [J].
Ahmed, A ;
Bragg, RA ;
Clayden, J ;
Lai, LW ;
McCarthy, C ;
Pink, JH ;
Westlund, N ;
Yasin, SA .
TETRAHEDRON, 1998, 54 (43) :13277-13294
[3]  
[Anonymous], 1999, ANGEW CHEM
[4]   STUDY OF BARRIERS TO ROTATION IN SOME HIGHLY SUBSTITUTED DIPHENYL ETHERS [J].
BERGMAN, JJ ;
CHANDLER, WD .
CANADIAN JOURNAL OF CHEMISTRY, 1972, 50 (03) :353-&
[5]   Synthesis of multiply ortho-substituted diaryl ethers via lithiation and oxidation of a dibenzosiloxane (phenoxasilin) [J].
Betson, MS ;
Clayden, J .
SYNLETT, 2006, (05) :745-746
[6]   Thermal atropisomerism of teicoplanin aglycon derivatives:: Preparation of the P,P,P and M,P,P atropisomers of the teicoplanin aglycon via selective equilibration of the DE ring system [J].
Boger, DL ;
Weng, JH ;
Miyazaki, S ;
McAtee, JJ ;
Castle, SL ;
Kim, SH ;
Mori, Y ;
Rogel, O ;
Strittmatter, H ;
Jin, Q .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (41) :10047-10055
[7]  
BOIDNARD S, 2000, ORG LETT, V2, P2459
[8]   Using symmetry to monitor geared bond rotation in aromatic amides by dynamic NMR [J].
Bragg, RA ;
Clayden, J .
ORGANIC LETTERS, 2000, 2 (21) :3351-3354
[9]  
Bragg RA, 2002, CHEM-EUR J, V8, P1279, DOI 10.1002/1521-3765(20020315)8:6<1279::AID-CHEM1279>3.0.CO
[10]  
2-7
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