Three Groups Good, Four Groups Bad? Atropisomerism in ortho-Substituted Diaryl Ethers†
Mark S. Betson Dr.
School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK, Fax: (+44) 161-275-4939
Search for more papers by this authorJonathan Clayden Prof.
School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK, Fax: (+44) 161-275-4939
Search for more papers by this authorChristopher P. Worrall
School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK, Fax: (+44) 161-275-4939
Search for more papers by this authorSimon Peace Dr.
GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts SG1 2NY, UK
Search for more papers by this authorMark S. Betson Dr.
School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK, Fax: (+44) 161-275-4939
Search for more papers by this authorJonathan Clayden Prof.
School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK, Fax: (+44) 161-275-4939
Search for more papers by this authorChristopher P. Worrall
School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK, Fax: (+44) 161-275-4939
Search for more papers by this authorSimon Peace Dr.
GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts SG1 2NY, UK
Search for more papers by this authorWe are grateful to the Leverhulme Trust, GlaxoSmithKline, and the EPSRC for funding this study.
Graphical Abstract
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 ArOAr 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.
Supporting Information
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