Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Catalytic Enantioselective Fluorination of α-Cyano Esters by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salts

  • Published : 2004.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Hudlicky, M.; Pavalath, A. E. Chemistry of Organic FluorineCompounds II; American Chemical Society, Washington DC, 1995.
  2. Hiyama, T.; Kanie, K.; Kusumoto, T.; Morizawa, Y.; Shimizu, M.Organofluorine Compounds: Chemistry and Applications; Springer-Verlag: Berlin, 2000.
  3. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661-692. https://doi.org/10.1016/S0957-4166(00)82374-5
  4. Takeuchi, Y.; Konishi, M.; Hori, H.; Takehashi, T.; Kometani,T.; Kirk, K. L. Chem. Commun. 1998, 365-366.
  5. Takeuchi, Y.;Konishi, M.; Hori, H.; Takehashi, T.; Kometani, T.; Kirk, K. L.Enantiomer 1999, 4, 339.
  6. Takeuchi, Y.; Fukushima, A.;Tanaka, Y.; Takeuchi, Y.; Kabuto, K.; Kabuto, C. Chem. Commun.2000, 787-788.
  7. Fugiwara, T.; Sasaki, M.; Omata, K.; Kabuto,C.; Kabuto, K.; Takeuchi, Y. Tetrahedron: Asymmetry 2004, 15,555-563. https://doi.org/10.1016/j.tetasy.2003.12.024
  8. Kusumoto, T.; Hiyama, T. In Enantiocontrolled Synthesis ofFluoro-organic Compounds; Soloshonok, V. A., Eds.; John Wiley& Sons: Chichester, 1999; pp 536-556.
  9. Kusumoto, T.; Hiyama, T. In Enantiocontrolled Synthesis ofFluoro-organic Compounds; Soloshonok, V. A., Eds.; John Wiley & Sons: Chichester, 1999; pp 536-556. https://doi.org/10.1021/ja002732x
  10. Shibata, N.; Suzuki, E.; Asahi, T.; Shiro,M. J. Am. Chem. Soc. 2001, 123, 7001-7009. https://doi.org/10.1021/ja010789t
  11. Shibata, N.;Ishimaru, T.; Suzuki, E.; Kirk, K. L. J. Org. Chem. 2003, 68,2494-2497. https://doi.org/10.1021/jo026792s
  12. Cahard, D.; Audouard, C.; Plaquevent, J.-C.;Toupet, L.; Roques, N. Tetrahedron Lett. 2001, 42, 1867-1869. https://doi.org/10.1016/S0040-4039(01)00017-X
  13. Baudequin, C.; Loubassou, J.-F.; Plaquevent, T.-C.; Cahard, D. J.Fluorin Chem. 2003, 122, 189-193. https://doi.org/10.1016/S0022-1139(03)00085-X
  14. Hintermann, L.; Togni, A.Angew. Chem., Int. Ed. Engl. 2000, 39, 4359-4362. https://doi.org/10.1002/1521-3773(20001201)39:23<4359::AID-ANIE4359>3.0.CO;2-P
  15. Hamashima,Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem.Soc. 2002, 124, 14530-14531. https://doi.org/10.1021/ja028464f
  16. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545-547. https://doi.org/10.1021/ol010281v
  17. Differding, E.; Lang, R. W. Tetrahedron Lett. 1988, 29, 6087-6090. https://doi.org/10.1016/S0040-4039(00)82271-6
  18. Davis, F. A.; Zhou, P.; Murphy, C. K.; Sundarababu, G.;Qi, H.; Przeslawski, R. M.; Chen, B.-C.; Carroll, P. J. J. Org.Chem. 1998, 63, 2273-2280. https://doi.org/10.1021/jo972045x
  19. Takeuchi, Y.; Suzuki, T.; Satoh,A.; Shiragami, T.; Shibata, N. J. Org. Chem. 1999, 64, 5708-5711. https://doi.org/10.1021/jo9904011
  20. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42,6299-6301. https://doi.org/10.1016/S0040-4039(01)01237-0
  21. Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57,8933-8938. https://doi.org/10.1016/S0040-4020(01)00891-2
  22. Kim, D. Y.; Choi, Y. J.; Park, H. Y.; Joung, C. U.;Koh, K. O.; Mang, J. Y.; Jung, K. Y. Synth. Commun. 2003, 33,435-443. https://doi.org/10.1081/SCC-120015774
  23. Kim, D. Y.; Kim, S. M.; Koh, K. O.; Mang, J. Y.;Lee, K. Bull. Korean Chem. Soc. 2003, 24, 1425-1426. https://doi.org/10.5012/bkcs.2003.24.10.1425
  24. Park, B. S.; Kim, D. Y.; Rosenthal, P. J.; Huh, S. C.; Lee, B. J.; Park, S.M.; Kim, J. E.; Kim, M. H.; Huh, T. L.; Choi, Y. J.; Suh, K. H.;Choi, W. S.; Lee, S. E. Bioorg. Med. Chem. Lett. 2002, 12, 1351-1355. https://doi.org/10.1016/S0960-894X(02)00173-7
  25. Kim, D. Y.; Huh, S. C. Bull. Korean Chem. Soc. 2004,25, 347-348. https://doi.org/10.5012/bkcs.2004.25.3.347
  26. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem.2004, 69, 6897-6899. https://doi.org/10.1021/jo0401772

Cited by

  1. Catalytic Enantioselective Fluorination of α-Chloro-β-keto Esters in the Presence of Chiral Nickel Complexes vol.352, pp.16, 2010, https://doi.org/10.1002/adsc.201000515
  2. A new entry to the construction of a quaternary carbon center having a fluorine atom – SN2′ reaction of γ-fluoroallylic alcohol derivatives with various cyanocuprates vol.10, pp.40, 2012, https://doi.org/10.1039/c2ob25718a
  3. Directing Group Strategy for Chiral Anion Phase-Transfer Fluorination of Allylic Alcohols vol.136, pp.37, 2014, https://doi.org/10.1021/ja507468u
  4. Organocatalysis in Enantioselective α-Functionalization of 2-Cyanoacetates vol.356, pp.16, 2014, https://doi.org/10.1002/adsc.201400404
  5. Thiourea-catalyzed Intramolecular Allylic Amination: Synthesis of Dihydroquinoline Derivatives vol.36, pp.1, 2015, https://doi.org/10.1002/bkcs.10014
  6. Organocatalytic Asymmetric Michael Addition of α-Fluoro β-Ketophosphonate to Nitroalkenes vol.36, pp.12, 2015, https://doi.org/10.1002/bkcs.10580
  7. Diastereo- and Enantioselective Conjugate Addition of α-Substituted Cyanoacetates to Maleimides Catalyzed by Binaphthyl-based Thiourea vol.36, pp.9, 2015, https://doi.org/10.1002/bkcs.10439
  8. Catalytic Enantioselective Fluorination of ?-Cyano Esters by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salts. vol.36, pp.12, 2005, https://doi.org/10.1002/chin.200512093
  9. Catalytic asymmetric fluorinations vol.4, pp.11, 2006, https://doi.org/10.1039/b603163c
  10. Organocatalyzed direct asymmetric α-halogenation of carbonyl compounds vol.7, pp.10, 2009, https://doi.org/10.1039/b901449g
  11. Catalysts: Direct Catalytic Asymmetric Addition of α-Fluoronitriles to Imines vol.58, pp.9, 2019, https://doi.org/10.1002/anie.201812673
  12. Dynamic Kinetic Resolution of α-Bromo Carboxylic Acid Derivatives in Asymmetric Nucleophilic Substitution with Chiral α-Amino Esters vol.26, pp.6, 2004, https://doi.org/10.5012/bkcs.2005.26.6.989
  13. Catalytic enantioselective fluorination of α-cyano acetates catalyzed by chiral palladium complexes vol.46, pp.17, 2004, https://doi.org/10.1016/j.tetlet.2005.02.164
  14. Asymmetric Electrophilic Fluorination of β-Keto Phosphonates in Ionic Liquid Media Catalyzed by Chiral Palladium Complexes vol.27, pp.3, 2006, https://doi.org/10.5012/bkcs.2006.27.3.423
  15. Asymmetric Michael Reaction of Malonate Derivatives with α, β-Unsaturated Ketones vol.27, pp.6, 2004, https://doi.org/10.5012/bkcs.2006.27.6.857
  16. Catalytic Asymmetric Fluorination of α-Chloro-β-ketoesters in the Presence of Chiral Palladium Complexes vol.28, pp.12, 2007, https://doi.org/10.5012/bkcs.2007.28.12.2191
  17. Catalytic Enantioselective Fluorination Reactions of α-Cyano Acetates and α-Cyanophosphonates Using Chiral Palladium Complexes vol.28, pp.12, 2004, https://doi.org/10.5012/bkcs.2007.28.12.2435
  18. DBFOX-Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones vol.4, pp.None, 2004, https://doi.org/10.3762/bjoc.4.16
  19. Enantioselective Electrophilic α-Amination of α-Cyanoketones Catalyzed by Chiral Nickel Complexes vol.29, pp.10, 2004, https://doi.org/10.5012/bkcs.2008.29.10.2036
  20. Enantioselective Fluorination of β-Keto Phosphonates and β-Ketoesters Catalyzed by Chiral Palladium Complexes vol.30, pp.4, 2004, https://doi.org/10.5012/bkcs.2009.30.4.829
  21. Palladium-catalyzed Asymmetric Mannich-type Reactions of α-Cyanoketones with N-Boc Aldimines vol.30, pp.7, 2004, https://doi.org/10.5012/bkcs.2009.30.7.1437
  22. Catalytic Asymmetric Electrophilic α-Amination of β-Ketoesters in the Presence of Chiral Nickel Complexes vol.30, pp.1, 2004, https://doi.org/10.5012/bkcs.2009.30.1.249
  23. Microwave-Assisted Organocatalytic Synthesis of Tetrahydroquinolines via Hydride Transfer and Cyclization vol.32, pp.5, 2004, https://doi.org/10.5012/bkcs.2011.32.5.1773
  24. Organocatalytic Enantioselective Michael Addition of α-Nitroacetate to α,β-Unsaturated Enones: A Route to Chiral γ-Nitro Ketones and δ-Keto Esters vol.32, pp.1, 2011, https://doi.org/10.5012/bkcs.2011.32.1.291
  25. Enantioselective Organocatalytic Synthesis of Fluorinated Molecules vol.17, pp.7, 2004, https://doi.org/10.1002/chem.201001546
  26. A convenient method for the synthesis of fluorinated α-cyanoacetatesviaphase-transfer catalysis vol.48, pp.15, 2004, https://doi.org/10.1080/00397911.2018.1473442
  27. Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs vol.118, pp.7, 2004, https://doi.org/10.1021/acs.chemrev.7b00778
  28. Achiral Trisubstituted Thioureas as Secondary Ligands to CuI Catalysts: Direct Catalytic Asymmetric Addition of α‐Fluoronitriles to Imines vol.131, pp.9, 2019, https://doi.org/10.1002/ange.201812673
  29. Synthesis of Fluoromethyl‐Substituted Cyclopentanones via Radical Fluorination and 1,2‐Alkyl Migration Cascade of Alkenyl Cyclobutanols vol.8, pp.5, 2004, https://doi.org/10.1002/ajoc.201900029
  30. Recent Advances in Catalytic Enantioselective Synthesis of Fluorinated α‐ and β‐Amino Acids vol.362, pp.22, 2020, https://doi.org/10.1002/adsc.202000966