Asymmetric synthesis of biaryl atropisomers by dynamic resolution on condensation of biaryl aldehydes with (−)-ephedrine or a proline-derived diamine

Scholarly Works

• Darwish, K. M.; Yassen, A. S. A.; Husseiny, E. M.; Hamed, M. I. A.; Helal, M. A. doi:10.1002/9783527844258.ch11
• Kolarovič, A.; Jakubec, P. State of the Art in Crystallization-Induced Diastereomer Transformations. Advanced Synthesis & Catalysis 2021, 363, 4110–4158. doi:10.1002/adsc.202100473
• Toenjes, S. T.; Gustafson, J. L. Atropisomerism in medicinal chemistry: challenges and opportunities. Future medicinal chemistry 2018, 10, 409–422. doi:10.4155/fmc-2017-0152
• Diemer, V.; Maury, J.; Le Bailly, B. A. F.; Webb, S. J.; Clayden, J. Dibenzazepinyl ureas as dual NMR and CD probes of helical screw-sense preference in conformationally equilibrating dynamic foldamers. Chemical communications (Cambridge, England) 2017, 53, 10768–10771. doi:10.1039/c7cc06427f
• Staniland, S.; Adams, R. W.; McDouall, J. J. W.; Maffucci, I.; Contini, A.; Grainger, D. M.; Turner, N. J.; Clayden, J. Biocatalytic Dynamic Kinetic Resolution for the Synthesis of Atropisomeric Biaryl N‐Oxide Lewis Base Catalysts. Angewandte Chemie 2016, 128, 10913–10917. doi:10.1002/ange.201605486
• Staniland, S.; Adams, R. W.; McDouall, J. J. W.; Maffucci, I.; Contini, A.; Grainger, D. M.; Turner, N. J.; Clayden, J. Biocatalytic Dynamic Kinetic Resolution for the Synthesis of Atropisomeric Biaryl N-Oxide Lewis Base Catalysts. Angewandte Chemie (International ed. in English) 2016, 55, 10755–10759. doi:10.1002/anie.201605486
• Staniland, S.; Yuan, B.; Giménez-Agulló, N.; Marcelli, T.; Willies, S. C.; Grainger, D. M.; Turner, N. J.; Clayden, J. Enzymatic desymmetrising redox reactions for the asymmetric synthesis of biaryl atropisomers. Chemistry (Weinheim an der Bergstrasse, Germany) 2014, 20, 13084–13088. doi:10.1002/chem.201404509
• Fischer, F.; Jungk, P.; Weding, N.; Spannenberg, A.; Ott, H.; Hapke, M. Diastereomeric Atropisomers from a Chiral Diyne by Cobalt(I)‐Catalyzed Cyclotrimerization. European Journal of Organic Chemistry 2012, 2012, 5828–5838. doi:10.1002/ejoc.201200402
• Page, A.; Clayden, J. Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers. Beilstein journal of organic chemistry 2011, 7, 1327–1333. doi:10.3762/bjoc.7.156
• Kamei, T.; Sato, A.; Iwasawa, T. Asymmetric Suzuki–Miyaura cross-coupling of aryl chlorides with enhancement of reaction time and catalyst turnover. Tetrahedron Letters 2011, 52, 2638–2641. doi:10.1016/j.tetlet.2011.03.051
• Yuan, B.; Page, A.; Worrall, C. P.; Escalettes, F.; Willies, S. C.; McDouall, J. J. W.; Turner, N. J.; Clayden, J. Biocatalytic Desymmetrization of an Atropisomer with both an Enantioselective Oxidase and Ketoreductases. Angewandte Chemie 2010, 122, 7164–7167. doi:10.1002/ange.201002580
• Yuan, B.; Page, A.; Worrall, C.; Escalettes, F.; Willies, S. C.; McDouall, J. J. W.; Turner, N. J.; Clayden, J. Biocatalytic Desymmetrization of an Atropisomer with both an Enantioselective Oxidase and Ketoreductases. Angewandte Chemie (International ed. in English) 2010, 49, 7010–7013. doi:10.1002/anie.201002580
• Clayden, J.; Senior, J.; Helliwell, M. Atropisomerism at C ? S Bonds: Asymmetric Synthesis of Diaryl Sulfones by Dynamic Resolution Under Thermodynamic Control. Angewandte Chemie (International ed. in English) 2009, 48, 6270–6273. doi:10.1002/anie.200901718
• Clayden, J.; Senior, J.; Helliwell, M. Atropisomerism at CS Bonds: Asymmetric Synthesis of Diaryl Sulfones by Dynamic Resolution Under Thermodynamic Control. Angewandte Chemie 2009, 121, 6388–6391. doi:10.1002/ange.200901718
• Clayden, J.; Turner, H. Enantiomerically enriched atropisomeric N,N′-diaryl ureas by oxidative kinetic resolution of their 2-sulfanyl derivatives. Tetrahedron Letters 2009, 50, 3216–3219. doi:10.1016/j.tetlet.2009.02.021

Explore citations to this article at