Bulletin of the Korean Chemical Society

  • 제29권11호
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  • Pages.2091-2092
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  • 2008
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Enantioselective α-Hydrazination of α-Fluoro-β-Ketoesters Catalyzed by Bifunctional Organocatalysts

  • 발행 : 2008.11.20
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참고문헌

  1. Ramachandran, P. V.; Ed. Asymmetric Fluoroorganic Chemistry: Synthesis, Application, and Future Directions, ACS Symposium Series 746; American Chemical Society: Washington, DC, 2000
  2. Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 104, 1 https://doi.org/10.1021/cr030685w
  3. Ibrahim, H.; Togni, A. Chem. Commun. 2004, 1147
  4. Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104, 6119 https://doi.org/10.1021/cr030143e
  5. France, S.; Weatherwax, A.; Lectka, T. Eur. J. Org. Chem. 2005, 475
  6. Qiu, X.-L.; Meng, W.-D.; Quing, F.-L. Tetrahedron 2004, 60, 6711 https://doi.org/10.1016/j.tet.2004.05.051
  7. Sutherland, A.; Willis, C. L. Nat. Prod. Rep. 2000, 17, 621 https://doi.org/10.1039/a707503k
  8. Kelly, N. M.; Sutherland, A.; Willis, C. L. Nat. Prod. Rep. 1997, 14, 205 https://doi.org/10.1039/np9971400205
  9. Dev, R.; Badet, B.; Meffre, P. Amino Acids 2003, 24, 245 https://doi.org/10.1007/s00726-002-0410-9
  10. Kukhar, V. P.; Soloshonok, V. A. Fluorine-Containing Amino Acids: Synthesis and Properties; Wiley: New York, 1995
  11. Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Biomedical Aspects of Fluorine Chemistry; Elsevier: Amsterdam, 1993
  12. Relimpio, A.; Slebe, J. C.; Martinez-Carrion, M. Biochem. Biophys. Res. Commun. 1975, 63, 625 https://doi.org/10.1016/S0006-291X(75)80430-X
  13. Bai, P.; Luo, L.; Peng, Z. Biochemistry 2000, 39, 372 https://doi.org/10.1021/bi992056f
  14. Kotha, S. Acc. Chem. Res. 2003, 36, 342 https://doi.org/10.1021/ar020147q
  15. Najera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584 https://doi.org/10.1021/cr050580o
  16. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4565 https://doi.org/10.1016/j.tetlet.2006.05.003
  17. Comelles, J.; Pericas, A.; Moreno-Manas, M.; Vallribera, A.; Drudis-Sole, G.; Lledos, A.; Parella, T.; Roglans, A.; Garcia- Grands, S.; Roces-Fernandez, L. J. Org. Chem. 2007, 72, 2077 https://doi.org/10.1021/jo0622678
  18. Mashiko, T.; Hara, K.; Tanaka, D.; Fujiwara, Y.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 11342 https://doi.org/10.1021/ja0752585
  19. Hasegawa, Y.; Watanabe, M.; Gridnev, I. D.; Ikariya, T. J. Am. Chem. Soc. 2008, 130, 2158 https://doi.org/10.1021/ja710273s
  20. Pihko, P. M.; Pohjakallio, A. Synlett 2004, 2115
  21. Xu, X.; Yabuta, T.; Yuan, P.; Takemoto, Y. Synlett 2006, 137
  22. Terada, M.; Nakano, M.; Ube, H. J. Am. Chem. Soc. 2006, 128, 16044 https://doi.org/10.1021/ja066808m
  23. Huber, D. P.; Stanek, K.; Togni, A. Tetrahedron: Asymmetry 2006, 17, 658 https://doi.org/10.1016/j.tetasy.2006.01.035
  24. Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2004, 43, 5138 https://doi.org/10.1002/anie.200400650
  25. Connon, S. J. Chem. Eur. J. 2006, 12, 5418 https://doi.org/10.1002/chem.200501076
  26. Tylor, M. S.; Jacobson, E. N. Angew. Chem. Int. Ed. 2006, 45, 1520 https://doi.org/10.1002/anie.200503132
  27. Connon, S. J. Angew. Chem. Int. Ed. 2006, 45, 3909 https://doi.org/10.1002/anie.200600529
  28. Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299 https://doi.org/10.1039/b511216h
  29. Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999 https://doi.org/10.1002/adsc.200606074
  30. Yu, X.; Wang, W. Chem. Asian J. 2008, 3, 516 https://doi.org/10.1002/asia.200700415
  31. Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527 https://doi.org/10.1016/j.tetlet.2008.07.041
  32. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545 https://doi.org/10.1021/ol010281v
  33. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897 https://doi.org/10.1021/jo0401772
  34. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309 https://doi.org/10.1021/ol050413a
  35. Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115 https://doi.org/10.1016/j.tetlet.2005.02.164
  36. Kim, S. M.; Kang, Y. K.; Lee, K.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2006, 27, 423 https://doi.org/10.5012/bkcs.2006.27.3.423
  37. Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135
  38. 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
  39. Kim, S. M.; Kang, Y. K.; Cho, M. J.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2007, 28, 2435 https://doi.org/10.5012/bkcs.2007.28.12.2435
  40. Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett 2008, 1821
  41. Connon, S. J. Chem. Commun. 2008, 2499

피인용 문헌

  1. ChemInform Abstract: Enantioselective α-Hydrazination of α-Fluoro-β-ketoesters Catalyzed by Bifunctional Organocatalysts vol.40, pp.12, 2009, https://doi.org/10.1002/chin.200912085
  2. Highly Enantioselective Amination Reactions of Fluorinated Keto Esters Catalyzed by Novel Chiral Guanidines Derived from Cinchona Alkaloids vol.352, pp.16, 2010, https://doi.org/10.1002/adsc.201000562
  3. Enantioselective organocatalytic α-heterofunctionalization of active methines vol.2, pp.2, 2012, https://doi.org/10.1039/C1RA00612F
  4. Highly Enantioselective Preparation of Fluorinated Phosphonates by Michael Addition of α-Fluoro-β-ketophosphonates to Nitroalkenes vol.3, pp.4, 2013, https://doi.org/10.1002/ajoc.201300211
  5. Asymmetric Michael addition of α-fluoro-α-nitroalkanes to nitroolefins: facile preparation of fluorinated amines and tetrahydropyrimidines vol.50, pp.66, 2014, https://doi.org/10.1039/C4CC03513E
  6. Asymmetric Michael addition of α-fluoro-α-nitro esters to nitroolefins: towards synthesis of α-fluoro-α-substituted amino acids vol.13, pp.8, 2015, https://doi.org/10.1039/C4OB02486A
  7. Thiourea-catalyzed Intramolecular Allylic Amination: Synthesis of Dihydroquinoline Derivatives vol.36, pp.1, 2015, https://doi.org/10.1002/bkcs.10014
  8. Recent Advances in Asymmetric Catalytic Methods for the Formation of Acyclic α,α-Disubstituted α-Amino Acids vol.80, pp.1, 2015, https://doi.org/10.1021/jo502408z
  9. Construction of Chiral α-Amino Quaternary Stereogenic Centers via Phase-Transfer Catalyzed Enantioselective α-Alkylation of α-Amidomalonates vol.80, pp.6, 2015, https://doi.org/10.1021/jo502791d
  10. Enantioselective Organocatalyzed Transformations of β-Ketoesters vol.116, pp.16, 2016, https://doi.org/10.1021/acs.chemrev.6b00156
  11. Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst vol.17, pp.6, 2012, https://doi.org/10.3390/molecules17067523
  12. Enantioselective Fluorination of β-Keto Phosphonates and β-Ketoesters Catalyzed by Chiral Palladium Complexes vol.30, pp.4, 2008, https://doi.org/10.5012/bkcs.2009.30.4.829
  13. Palladium-catalyzed Asymmetric Mannich-type Reactions of α-Cyanoketones with N-Boc Aldimines vol.30, pp.7, 2008, https://doi.org/10.5012/bkcs.2009.30.7.1437
  14. Enantioselective Conjugate Addition of Fluoromalonate to Nitroalkenes Catalyzed by Chiral Nickel Complexes vol.30, pp.7, 2008, https://doi.org/10.5012/bkcs.2009.30.7.1439
  15. Organocatalytic Asymmetric Michael Addition of β-Ketoesters to Nitroalkenes vol.30, pp.7, 2008, https://doi.org/10.5012/bkcs.2009.30.7.1441
  16. Catalytic Asymmetric Electrophilic α-Amination of β-Ketoesters in the Presence of Chiral Nickel Complexes vol.30, pp.1, 2008, https://doi.org/10.5012/bkcs.2009.30.1.249
  17. Catalytic enantioselective conjugate addition of aromatic amines to fumarate derivatives: asymmetric synthesis of aspartic acid derivatives vol.65, pp.29, 2009, https://doi.org/10.1016/j.tet.2009.05.037
  18. Organocatalytic Asymmetric Friedel-Crafts Alkylation to γ-Hydroxy α,β-Unsaturated Aldehyde vol.30, pp.11, 2008, https://doi.org/10.5012/bkcs.2009.30.11.2519
  19. Microwave-Assisted Organocatalytic Synthesis of Tetrahydroquinolines via Hydride Transfer and Cyclization vol.32, pp.5, 2008, https://doi.org/10.5012/bkcs.2011.32.5.1773
  20. 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
  21. Asymmetric Mannich-type Reactions of Fluorinated Ketoesters with Binaphthyl-Modified Thiourea Catalysts vol.32, pp.4, 2008, https://doi.org/10.5012/bkcs.2011.32.4.1195
  22. Organocatalytic Asymmetric Conjugate Addition of 3-Alkyl-Substituted Oxindoles to Vinyl Ketones vol.33, pp.10, 2008, https://doi.org/10.5012/bkcs.2012.33.10.3171
  23. Organocatalytic enantioselective decarboxylative Michael addition of β-ketoacids to α,β-unsaturated ketones vol.3, pp.5, 2008, https://doi.org/10.1039/c2ra21945j
  24. Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to Benzylidenemalonitriles vol.35, pp.1, 2008, https://doi.org/10.5012/bkcs.2014.35.1.98
  25. Highly Enantioselective Michael Addition of 2‐Fluoro‐1,3‐diketones to Nitroalkenes vol.2015, pp.2, 2008, https://doi.org/10.1002/ejoc.201403361
  26. Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination vol.16, pp.None, 2008, https://doi.org/10.3762/bjoc.16.163
  27. 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