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

Ann Bracegirdle, Jonathan Clayden and Lai Wah Lai
Beilstein J. Org. Chem. 2008, 4, No. 47. https://doi.org/10.3762/bjoc.4.47

Supporting Information

Procedures for the synthesis, and characterisation data, of the remaining compounds reported in this paper.

Supporting Information File 1: Full experimental data for all new compounds reported in the paper.
Format: DOC Size: 122.0 KB Download

Cite the Following Article

Asymmetric synthesis of biaryl atropisomers by dynamic resolution on condensation of biaryl aldehydes with (−)-ephedrine or a proline-derived diamine
Ann Bracegirdle, Jonathan Clayden and Lai Wah Lai
Beilstein J. Org. Chem. 2008, 4, No. 47. https://doi.org/10.3762/bjoc.4.47

How to Cite

Bracegirdle, A.; Clayden, J.; Lai, L. W. Beilstein J. Org. Chem. 2008, 4, No. 47. doi:10.3762/bjoc.4.47

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • 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
Other Beilstein-Institut Open Science Activities