DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones

Takehisa Ishimaru, Norio Shibata, Dhande Sudhakar Reddy, Takao Horikawa, Shuichi Nakamura and Takeshi Toru
Beilstein J. Org. Chem. 2008, 4, No. 16. https://doi.org/10.3762/bjoc.4.16

Supporting Information

Supporting Information File 1: Experimental methods. General methods, general procedure for the enantioselective catalytic fluorination, spectral data of 2, copies of 1H, 13C and 19F-NMRs and HPLC charts of 2
Format: DOC Size: 7.2 MB Download

Cite the Following Article

DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones
Takehisa Ishimaru, Norio Shibata, Dhande Sudhakar Reddy, Takao Horikawa, Shuichi Nakamura and Takeshi Toru
Beilstein J. Org. Chem. 2008, 4, No. 16. https://doi.org/10.3762/bjoc.4.16

How to Cite

Ishimaru, T.; Shibata, N.; Reddy, D. S.; Horikawa, T.; Nakamura, S.; Toru, T. Beilstein J. Org. Chem. 2008, 4, No. 16. doi:10.3762/bjoc.4.16

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

  • Ishihara, K. 触媒的エナンチオ選択的α-ハロゲン化反応に潜むハロゲン結合の影響. Journal of Synthetic Organic Chemistry, Japan 2023, 81, 474–482. doi:10.5059/yukigoseikyokaishi.81.474
  • Remete, A. M.; Nonn, M.; Escorihuela, J.; Fustero, S.; Kiss, L. Asymmetric Methods for Carbon-Fluorine Bond Formation. European Journal of Organic Chemistry 2021, 2021, 5946–5974. doi:10.1002/ejoc.202101094
  • Grell, Y.; Xie, X.; Ivlev, S. I.; Meggers, E. Enantioselective α-Fluorination and α-Chlorination of N-Acyl Pyrazoles Catalyzed by a Non-C2-Symmetric Chiral-at-Rhodium Catalyst. ACS Catalysis 2021, 11, 11396–11406. doi:10.1021/acscatal.1c02901
  • Connon, R.; Roche, B.; Rokade, B. V.; Guiry, P. J. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis. Chemical reviews 2021, 121, 6373–6521. doi:10.1021/acs.chemrev.0c00844
  • Ishihara, K.; Nishimura, K.; Yamakawa, K. Enantio‐ and Site‐Selective α‐Fluorination of N‐Acyl 3,5‐Dimethylpyrazoles Catalyzed by Chiral π–CuII Complexes. Angewandte Chemie 2020, 132, 17794–17800. doi:10.1002/ange.202007403
  • Ishihara, K.; Nishimura, K.; Yamakawa, K. Enantio- and Site-Selective α-Fluorination of N-Acyl 3,5-Dimethylpyrazoles Catalyzed by Chiral π–CuII Complexes. Angewandte Chemie (International ed. in English) 2020, 59, 17641–17647. doi:10.1002/anie.202007403
  • doi:10.1002/9783527809080.cataz10057
  • Huang, W.; Yao, Y.; Xu, Y.-J.; Lu, C.-D. Diastereoselective α-Fluorination of N- tert-Butanesulfinyl Imidates. The Journal of organic chemistry 2018, 83, 14777–14785. doi:10.1021/acs.joc.8b02375
  • Itoh, K.; Sibi, M. P. Dibenzofuran-4,6-bis(oxazoline) (DBFOX). A novel trans-chelating bis(oxazoline) ligand for asymmetric reactions. Organic & biomolecular chemistry 2018, 16, 5551–5565. doi:10.1039/c8ob01010b
  • Zhu, Y.; Han, J.; Wang, J.; Shibata, N.; Sodeoka, M.; Soloshonok, V. A.; Coelho, J. A. S.; Toste, F. D. Modern Approaches for Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs. Chemical reviews 2018, 118, 3887–3964. doi:10.1021/acs.chemrev.7b00778
  • Thornbury, R. T.; Schäfer, G.; Toste, F. Catalytic Enantioselective Fluorination. Modern Synthesis Processes and Reactivity of Fluorinated Compounds; Elsevier, 2017; pp 223–263. doi:10.1016/b978-0-12-803740-9.00009-3
  • Enantioselective Nickel-Catalysed α-Heterofunctionalisation, and α-Arylation/Alkylation Reactions of Carbonyl Compounds. Enantioselective Nickel-Catalysed Transformations; The Royal Society of Chemistry, 2016; pp 232–260. doi:10.1039/9781782626701-00232
  • Champagne, P. A.; Desroches, J.; Hamel, J. D.; Vandamme, M.; Paquin, J.-F. Monofluorination of Organic Compounds: 10 Years of Innovation. Chemical reviews 2015, 115, 9073–9174. doi:10.1021/cr500706a
  • Yang, X.; Wu, T.; Phipps, R. J.; Toste, F. D. Advances in catalytic enantioselective fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation reactions. Chemical reviews 2014, 115, 826–870. doi:10.1021/cr500277b
  • Differding, E.; Poss, A. J.; Cahard, D.; Shibata, N. Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, Ltd, 2013; pp 1–17. doi:10.1002/047084289x.rf011.pub3
  • Chen, Z.-M.; Yang, B.-M.; Chen, Z.-H.; Zhang, Q.-W.; Wang, M.; Tu, Y.-Q. Organocatalytic asymmetric fluorination/semipinacol rearrangement: an efficient approach to chiral β-fluoroketones. Chemistry (Weinheim an der Bergstrasse, Germany) 2012, 18, 12950–12954. doi:10.1002/chem.201202444
  • Suzuki, S.; Kitamura, Y.; Lectard, S.; Hamashima, Y.; Sodeoka, M. Catalytic Asymmetric Mono‐Fluorination of α‐Keto Esters: Synthesis of Optically Active β‐Fluoro‐α‐Hydroxy and β‐Fluoro‐α‐Amino Acid Derivatives. Angewandte Chemie 2012, 124, 4659–4663. doi:10.1002/ange.201201303
  • Suzuki, S.; Kitamura, Y.; Lectard, S.; Hamashima, Y.; Sodeoka, M. Catalytic asymmetric mono-fluorination of α-keto esters: synthesis of optically active β-fluoro-α-hydroxy and β-fluoro-α-amino acid derivatives. Angewandte Chemie (International ed. in English) 2012, 51, 4581–4585. doi:10.1002/anie.201201303
  • Suzuki, S.; Tokunaga, E.; Reddy, D. S.; Matsumoto, T.; Shiro, M.; Shibata, N. Enantioselective 5-endo-dig Carbocyclization of β-Ketoesters with Internal Alkynes Employing a Four-Component Catalyst System. Angewandte Chemie (International ed. in English) 2012, 51, 4131–4135. doi:10.1002/anie.201201060
  • Suzuki, S.; Tokunaga, E.; Reddy, D. S.; Matsumoto, T.; Shiro, M.; Shibata, N. Enantioselective 5‐endo‐dig Carbocyclization of β‐Ketoesters with Internal Alkynes Employing a Four‐Component Catalyst System. Angewandte Chemie 2012, 124, 4207–4211. doi:10.1002/ange.201201060
Other Beilstein-Institut Open Science Activities