Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Catalytic Enantioselective Fluorination of α-Cyanosulfones in the Presence of Chiral Palladium Complexes

  • Received : 2012.04.06
  • Accepted : 2012.05.17
  • Published : 2012.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Fernandez, M.; Caballero, J. Bioorg. Med. Chem. 2007, 15, 6298. https://doi.org/10.1016/j.bmc.2007.06.014
  2. Cid, M. B.; Lopez-Cantarero, J.; Duce, S.; Ruano, J. L. G. J. Org. Chem. 2009, 74, 431. https://doi.org/10.1021/jo801968p
  3. Alonso, D. A.; Costa, A.; Mancheno, B.; Najera, C. Tetrahedron 1997, 53, 4791. https://doi.org/10.1016/S0040-4020(97)00163-4
  4. Giovannini, R.; Petrini, M. Synlett 1997, 90.
  5. Ender, D.; Signore, G. D. Heterocycles 2004, 64, 101. https://doi.org/10.3987/COM-04-S(P)3
  6. Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661. https://doi.org/10.1016/S0957-4166(00)82374-5
  7. Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 104, 1. https://doi.org/10.1021/cr030685w
  8. Ibrahim, H.; Togni, A. Chem. Commun. 2004, 1147.
  9. France, S.; Weatherwax, A.; Lectka, T. Eur. J. Org. Chem. 2005, 475.
  10. Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1. https://doi.org/10.1021/cr800221v
  11. Kang, Y. K.; Kim, D. Y. Curr. Org. Chem. 2010, 14, 917. https://doi.org/10.2174/138527210791111768
  12. Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. 2000, 39, 4359. https://doi.org/10.1002/1521-3773(20001201)39:23<4359::AID-ANIE4359>3.0.CO;2-P
  13. Kim, D. Y.; Park E. J. Org. Lett. 2002, 4, 545. https://doi.org/10.1021/ol010281v
  14. Hamashima, Y.; Yagi, K.; Takano, H.; Tamas, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530. https://doi.org/10.1021/ja028464f
  15. Cho, M. J.; Kang, Y. K.; Lee, N. R.; Kim, D. Y. Bull. Korean Chem. Soc. 2007, 28, 2191. https://doi.org/10.5012/bkcs.2007.28.12.2191
  16. Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115. https://doi.org/10.1016/j.tetlet.2005.02.164
  17. Kim, S. M.; Kang, Y. K.; Cho, M. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2007, 28, 2435. https://doi.org/10.5012/bkcs.2007.28.12.2435
  18. Bernardi, L.; Jorgensen, K. A. Chem. Commun. 2005, 1324.
  19. Hamashima, Y.; Suzuki, T.; Shimura, Y.; Shimizu, T.; Umebayashi, N.: Tamura, T.; Sasamoto, N.; Sodeoka, M. Tetrahedron Lett. 2005, 46, 1447. https://doi.org/10.1016/j.tetlet.2005.01.018
  20. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309. https://doi.org/10.1021/ol050413a
  21. Kang, Y. K; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135.
  22. Moriyama, K.; Hamashima, Y.; Sodeoka, M. Synlett 2007, 1139.
  23. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897. https://doi.org/10.1021/jo0401772
  24. Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779. https://doi.org/10.1002/adsc.200900268
  25. Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847. https://doi.org/10.1021/ja103786c
  26. Kang, S. H.; Kim, D. Y. Adv. Synth. Catal. 2010, 352, 2783. https://doi.org/10.1002/adsc.201000515
  27. Kang, S. H.; Kwon, B. K.; Kim, D. Y. Tetrahedron Lett. 2011, 52, 3247. https://doi.org/10.1016/j.tetlet.2011.04.084
  28. Kang, Y. K.; Suh, K. H.; Kim, D. Y. Synlett 2011, 1125.
  29. Lee, H. J.; Chae, Y. M.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 2875. https://doi.org/10.5012/bkcs.2011.32.8.2875
  30. Lee, H. J.; Kang, S. H.; Kim, D. Y. Synlett 2011, 1559.
  31. Kang, Y. K.; Yoon, S. J.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 1195.
  32. Yoon, S. J.; Kang, Y. K.; Kim, D. Y. Synlett 2011, 420.
  33. Lee, H. J.; Kang, S. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 1125. https://doi.org/10.5012/bkcs.2011.32.4.1125
  34. Lee, H. J.; Kim, J. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 785. https://doi.org/10.5012/bkcs.2011.32.3.785
  35. Moon, H. W.; Kim, D. Y. Bull. Korean Chem. Soc. 2011, 32, 291. https://doi.org/10.5012/bkcs.2011.32.1.291
  36. Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett 2008, 1821.
  37. Kim, E. J.; Kang, Y. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1437. https://doi.org/10.5012/bkcs.2009.30.7.1437
  38. Lee, N. R.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 829. https://doi.org/10.5012/bkcs.2009.30.4.829
  39. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2011, 52, 2356. https://doi.org/10.1016/j.tetlet.2011.02.087

Cited by

  1. Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinone to β,γ-Unsaturated α-Keto Esters Catalyzed by Binaphthyl-Modified Squaramide vol.34, pp.6, 2013, https://doi.org/10.5012/bkcs.2013.34.6.1619
  2. Organocatalytic Asymmetric Michael Addition of 4-Hydroxycoumarin to β,γ-Unsaturated α-Keto Esters vol.34, pp.6, 2013, https://doi.org/10.5012/bkcs.2013.34.6.1623
  3. Enantioselective Direct α-Amination of Aromatic Ketones Catalyzed by Binaphthyl-Modified Primary Amine vol.34, pp.7, 2013, https://doi.org/10.5012/bkcs.2013.34.7.1955
  4. Organocatalytic Enantioselective Michael Addition of Silyl Malonate to α,β-Unsaturated Enones: One-pot Synthesis of Chiral δ-Keto Esters vol.34, pp.9, 2013, https://doi.org/10.5012/bkcs.2013.34.9.2569
  5. Monofluorination of Organic Compounds: 10 Years of Innovation vol.115, pp.17, 2015, https://doi.org/10.1021/cr500706a
  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. Organocatalytic enantioselective decarboxylative Michael addition of β-ketoacids to α,β-unsaturated ketones vol.3, pp.5, 2012, https://doi.org/10.1039/c2ra21945j
  9. Organocatalytic Enantioselective Friedel-Crafts Reaction of Naphthol with β,γ-Unsaturated α-Keto Esters vol.34, pp.12, 2012, https://doi.org/10.5012/bkcs.2013.34.12.3539
  10. Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to Benzylidenemalonitriles vol.35, pp.1, 2012, https://doi.org/10.5012/bkcs.2014.35.1.98
  11. Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs vol.118, pp.7, 2012, https://doi.org/10.1021/acs.chemrev.7b00778
  12. Enantioselective Organocatalytic Mannich Reaction and Fluorination Sequence of Pyrazolones to Isatin‐derived Ketimines vol.39, pp.12, 2018, https://doi.org/10.1002/bkcs.11625