Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution

Kazutaka Shibatomi, Takuya Okimi, Yoshiyuki Abe, Akira Narayama, Nami Nakamura and Seiji Iwasa
Beilstein J. Org. Chem. 2014, 10, 323–331. https://doi.org/10.3762/bjoc.10.30

Cite the Following Article

Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution
Kazutaka Shibatomi, Takuya Okimi, Yoshiyuki Abe, Akira Narayama, Nami Nakamura and Seiji Iwasa
Beilstein J. Org. Chem. 2014, 10, 323–331. https://doi.org/10.3762/bjoc.10.30

How to Cite

Shibatomi, K.; Okimi, T.; Abe, Y.; Narayama, A.; Nakamura, N.; Iwasa, S. Beilstein J. Org. Chem. 2014, 10, 323–331. doi:10.3762/bjoc.10.30

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

  • Hikawa, R.; Shimogaki, M.; Kano, T. Construction of three contiguous stereocenters through amine-catalyzed asymmetric aldol reactions. Chemical communications (Cambridge, England) 2023, 59, 8424–8427. doi:10.1039/d3cc01606d
  • Shibatomi, K. Organocatalytic Synthesis of Chiral Halogenated Compounds. Chemical record (New York, N.Y.) 2023, 23, e202300061. doi:10.1002/tcr.202300061
  • Noman, M. A. A.; Huang, D. S.; Coulup, S. K.; Syeda, S. S.; Henry; Wong, L.; Georg, G. I. Cytotoxicity of phenylpironetin analogs and the metabolic fate of pironetin and phenylpironetin. Bioorganic chemistry 2022, 125, 105915. doi:10.1016/j.bioorg.2022.105915
  • 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
  • Triandafillidi, I.; Voutyritsa, E.; Kokotos, C. G. Recent advances in reactions promoted by amino acids and oligopeptides. Physical Sciences Reviews 2020, 5, 29–84. doi:10.1515/psr-2018-0086
  • Takeshima, A.; Shimogaki, M.; Kano, T.; Maruoka, K. Development of Ketone-Based Brominating Agents (KBA) for the Practical Asymmetric α-Bromination of Aldehydes Catalyzed by Tritylpyrrolidine. ACS Catalysis 2020, 10, 5959–5963. doi:10.1021/acscatal.0c01596
  • Karabiyikoglu, S.; Brethomé, A. V.; Palacin, T.; Paton, R. S.; Fletcher, S. P. Enantiomerically enriched tetrahydropyridine allyl chlorides. Chemical Science 2020, 11, 4125–4130. doi:10.1039/d0sc00377h
  • Farid, U.; Aiello, M. L.; Connon, S. J. Highly Enantioselective Catalytic Kinetic Resolution of α-Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides. Chemistry (Weinheim an der Bergstrasse, Germany) 2019, 25, 10074–10079. doi:10.1002/chem.201902422
  • Shibatomi, K. Enantioselective Fluorination. Late-Stage Fluorination of Bioactive Molecules and Biologically-Relevant Substrates; Elsevier, 2019; pp 137–158. doi:10.1016/b978-0-12-812958-6.00004-5
  • 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
  • De Schutter, C.; Sari, O.; Coats, S. J.; Amblard, F.; Schinazi, R. F. Synthesis of (2S)-2-Chloro-2-fluororibolactone via Stereoselective Electrophilic Fluorination. The Journal of organic chemistry 2017, 82, 13171–13178. doi:10.1021/acs.joc.7b02245
  • Szőllősi, G.; Kovács, L.; Kozma, V.; Kolcsár, V. J. Asymmetric Michael addition catalyzed by a cinchona alkaloid derivative non-covalently immobilized on layered inorganic supports. Reaction Kinetics, Mechanisms and Catalysis 2017, 121, 293–306. doi:10.1007/s11144-017-1144-8
  • Emma, M. G.; Lombardo, M.; Trombini, C.; Quintavalla, A. The Organocatalytic α-Fluorination of Chiral γ-Nitroaldehydes: the Challenge of Facing the Construction of a Quaternary Fluorinated Stereocenter. European Journal of Organic Chemistry 2016, 2016, 3223–3232. doi:10.1002/ejoc.201600378
  • Fjelbye, K.; Marigo, M.; Clausen, R. P.; Juhl, K. Diastereodivergent Access to Syn and Anti 3,4-Substituted β-Fluoropyrrolidines: Enhancing or Reversing Substrate Preference. Organic letters 2016, 18, 1170–1173. doi:10.1021/acs.orglett.6b00293
  • Shibatomi, K.; Kitahara, K.; Okimi, T.; Abe, Y.; Iwasa, S. Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C–F bond cleavage. Chemical science 2015, 7, 1388–1392. doi:10.1039/c5sc03486h
  • Gurubrahamam, R.; Cheng, Y. S.; Huang, W. Y.; Chen, K. Recent Advances in Organocatalytic Kinetic Resolution for the Synthesis of Functionalized Products. ChemCatChem 2015, 8, 86–96. doi:10.1002/cctc.201500455
  • 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
  • Lin, J.-H.; Xiao, J.-C. Recent advances in asymmetric fluorination and fluoroalkylation reactions via organocatalysis. Tetrahedron Letters 2014, 55, 6147–6155. doi:10.1016/j.tetlet.2014.09.031
  • 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
  • Shibatomi, K. Highly Enantioselective Synthesis of Halogenated Compounds Utilizing Lewis Acid or Organocatalyst. Journal of Synthetic Organic Chemistry, Japan 2014, 72, 232–245. doi:10.5059/yukigoseikyokaishi.72.232
Other Beilstein-Institut Open Science Activities