Bulletin of the Korean Chemical Society

  • 제24권10호
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  • Pages.1425-1426
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  • 2003
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Enantioselective Michael Reaction of Fluoromalonates and Chalcones by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salt

  • 발행 : 2003.10.20
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참고문헌

  1. Leonard, J.Contemp. Org. Synth. 1994, 1, 387. https://doi.org/10.1039/co9940100387
  2. Perlmutter, P. ConjugateAddition Reactions in Organic Synthesis; Pergamon: Oxford,1992.
  3. Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92,771. https://doi.org/10.1021/cr00013a002
  4. Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki,M. Angew. Chem. Int. Ed. Engl. 1996, 35, 104. https://doi.org/10.1002/anie.199601041
  5. Kim, Y. S.;Matsunaga, S.; Das, J.; Sekine, A.; Ohshima, T.; Shibasaki, M. J.Am. Chem. Soc. 2000, 122, 6506. https://doi.org/10.1021/ja001036u
  6. Yamaguchi, M.; Shiraishi,T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. https://doi.org/10.1021/jo960216c
  7. Hanessian, S.;Pham, V. Org. Lett. 2000, 2, 2975. https://doi.org/10.1021/ol000170g
  8. Narasimhan, S.; Balakumar,V. R.; Radhakrishnan, V. Tetrahedron Lett. 2001, 42, 719. https://doi.org/10.1016/S0040-4039(00)01986-9
  9. Sundarajan, G.; Prabagaran, N. Org. Lett. 2001, 3, 389. https://doi.org/10.1021/ol006898e
  10. Perrard, T.; Plaquevent, L.-C.; Desmurs, J.-R.; Hebrault, D. Org.Lett. 2000, 2, 2959. https://doi.org/10.1021/ol006207e
  11. Dehmlow, E. V. and S. S. Phase Transfer Catalysis, 3rd Ed.;VCH: Weinheim, 1993.
  12. Goldberg, Y. Phase Transfer Catalysis:Selected Problems and Application; Gordon & Breach SciencePubl.: Reading, 1992.
  13. Starks, C. M.; Liotta, C. L.; Halpern, M.Phase Transfer Catalysis: Fundamentals, Applications, and IndustrialPerspectives; Chapman & Hall: New York, 1994.
  14. Shioiri, T.Chiral Phase Transfer Catalysis, Chapter 14 in Handbook ofPhase Transfer Catalysis; Sasson, Y., Neumann, R., Eds.; BlackieAcademic & Professional: London, 1997.
  15. O'Donnell, M. J.Asymmetric Phase Transfer Reactions, Chapter 10 in CatalyticAsymmetric Synthesis; Ojima, I., Eds.; Wiley-VCH: 2000.
  16. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. https://doi.org/10.1021/ja973174y
  17. Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem.Soc. 1998, 120, 13000. https://doi.org/10.1021/ja9835739
  18. Corey, E. J.; Noe, M. C.; Xu, F.Tetrahedron Lett. 1998, 39, 5347. https://doi.org/10.1016/S0040-4039(98)01067-3
  19. Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 39, 3843.
  20. Corey, E. J.; Zhang, F.-Y. Org. Lett 1999, 1, 1287. https://doi.org/10.1021/ol990964z
  21. Zhang, F.-Y;Corey, E. J. Org. Lett. 2000, 2, 1097. https://doi.org/10.1021/ol0056527
  22. Corey, E. J.; Zhang, F.-Y.Angew. Chem., Intl. Ed. 1999, 38, 1931. https://doi.org/10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO;2-4
  23. Lygo, B.; Wainwright,P. G. Tetrahedron Lett. 1997, 38, 8595. https://doi.org/10.1016/S0040-4039(97)10293-3
  24. Lygo, B.; Wainwright,P. G. Tetrahedron Lett. 1998, 39, 1599. https://doi.org/10.1016/S0040-4039(97)10779-1
  25. Lygo, B.; Crosby, J.;Peterson, J. A. Tetrahedron Lett. 1999, 40, 8671. https://doi.org/10.1016/S0040-4039(99)01836-5
  26. Lygo, B.;Wainwright, P. G. Tetrahedron 1999, 55, 6289. https://doi.org/10.1016/S0040-4020(99)00205-7
  27. Oku, M.; Arai,S.; Katayama, K.; Shioiri, T. Synlett 2000, 493.
  28. Arai, S.,Shirai, Y.; Ishida, T.; Shioiri, T. Tetrahedron 1999, 55, 6375. https://doi.org/10.1016/S0040-4020(99)00213-6
  29. Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39,2997. https://doi.org/10.1016/S0040-4039(98)00442-0
  30. Park, H.-g.; Jeong, B.-s.; Yoo, M.-s.; Lee, J.-h.; Park, B.-s.; Kim, M. G.; Jew, S.-s. Tetrahedron Lett. 2003, 44, 3497. https://doi.org/10.1016/S0040-4039(03)00687-7
  31. Jew, S.-s.; Yoo, M.-s.; Jeong, B.-s.; Park, I. Y.; Park, H.-g. Org.Lett. 2002, 4, 4245. https://doi.org/10.1021/ol0267679
  32. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. https://doi.org/10.1021/ol010281v
  33. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42,6299. https://doi.org/10.1016/S0040-4039(01)01237-0
  34. Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933. https://doi.org/10.1016/S0040-4020(01)00891-2
  35. 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. https://doi.org/10.1081/SCC-120015774

피인용 문헌

  1. Enantioselective Michael Addition Reactions vol.43, pp.1, 2011, https://doi.org/10.1080/00304948.2011.547102
  2. Asymmetric Conjugate Addition of 1-Fluoro-1-nitro(phenylsulfonyl)methane to Chalcones Catalyzed by Binaphthyl-Derived Organocatalyst vol.33, pp.9, 2012, https://doi.org/10.5012/bkcs.2012.33.9.2845
  3. Enantioselective One-Pot Synthesis of Ring-Fused Tetrahydroquinolines via Aerobic Oxidation and 1,5-Hydride Transfer/Cyclization Sequences vol.16, pp.20, 2014, https://doi.org/10.1021/ol502575f
  4. 2-Fluoromalonate Esters: Fluoroaliphatic Building Blocks for the Life Sciences vol.18, pp.8, 2014, https://doi.org/10.1021/op500141c
  5. Asymmetric Synthesis of Tetrahydroquinolines via Saegusa-type Oxidative Enamine Catalysis/1,5-Hydride Transfer/Cyclization Sequences vol.3, pp.4, 2014, https://doi.org/10.1002/ajoc.201400022
  6. Fluorine gas for life science syntheses: green metrics to assess selective direct fluorination for the synthesis of 2-fluoromalonate esters vol.17, pp.5, 2015, https://doi.org/10.1039/C5GC00402K
  7. Organocatalytic Asymmetric Michael Addition of α-Fluoro β-Ketophosphonate to Nitroalkenes vol.36, pp.12, 2015, https://doi.org/10.1002/bkcs.10580
  8. Organocatalytic Enantioselective Conjugate Addition of 3-Fluorooxindoles to Vinyl Sulfone vol.36, pp.5, 2015, https://doi.org/10.1002/bkcs.10263
  9. Diastereo- and Enantioselective Conjugate Addition of 3-Chlorooxindoles to Nitroalkenes Catalyzed by Binaphthyl-modified Organocatalyst vol.36, pp.5, 2015, https://doi.org/10.1002/bkcs.10264
  10. Catalytic Enantioselective Desymmetrization of meso-Aziridines with Fluoromalonates vol.94, pp.7, 2017, https://doi.org/10.3987/COM-17-13725
  11. Highly Diastereo- and Enantioselective Organocatalyzed Michael/Oxa-Michael Sequence: Asymmetric Synthesis of Pyranonaphthoquinone Derivatives vol.39, pp.10, 2018, https://doi.org/10.1002/bkcs.11566
  12. Asymmetric Michael Addition of Pyrazolones to β,γ-Unsaturated α-Keto Esters Catalyzed by Binaphthyl-modified Thiourea vol.39, pp.4, 2018, https://doi.org/10.1002/bkcs.11425
  13. Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes vol.53, pp.1, 2010, https://doi.org/10.1007/s11426-010-0031-1
  14. Catalytic Enantioselective Fluorination of α-Cyano Esters by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salts vol.25, pp.10, 2004, https://doi.org/10.5012/bkcs.2004.25.10.1451
  15. Enantioselective Michael Reaction of Fluoromalonates and Chalcones by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salt. vol.35, pp.8, 2003, https://doi.org/10.1002/chin.200408022
  16. Poly(ethylene glycol) Supported Chiral Quaternary Ammonium Salts as Phase-Transfer Catalysts for Catalytic Enantioselective Synthesis of α-Amino Acids vol.25, pp.3, 2003, https://doi.org/10.5012/bkcs.2004.25.3.347
  17. Enantioselective Alkylation of &bgr;-Keto Esters by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salts vol.69, pp.20, 2004, https://doi.org/10.1021/jo0401772
  18. 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
  19. Asymmetric Michael Reaction of Malonate Derivatives with α, β-Unsaturated Ketones vol.27, pp.6, 2003, https://doi.org/10.5012/bkcs.2006.27.6.857
  20. 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
  21. Catalytic Enantioselective Fluorination Reactions of α-Cyano Acetates and α-Cyanophosphonates Using Chiral Palladium Complexes vol.28, pp.12, 2003, https://doi.org/10.5012/bkcs.2007.28.12.2435
  22. Enantioselective Conjugate Addition of Fluoromalonate to Nitroalkenes Catalyzed by Chiral Nickel Complexes vol.30, pp.7, 2003, https://doi.org/10.5012/bkcs.2009.30.7.1439
  23. Highly enantioselective conjugate addition of fluoromalonates to nitroalkenes using bifunctional organocatalysts vol.130, pp.8, 2003, https://doi.org/10.1016/j.jfluchem.2009.06.002
  24. Highly Enantioselective Addition of 1-Fluoro-1-nitro(phenylsulfonyl)methane to α,β-Unsaturated Aldehydes vol.2010, pp.28, 2003, https://doi.org/10.1002/ejoc.201000851
  25. Microwave-Assisted Organocatalytic Synthesis of Tetrahydroquinolines via Hydride Transfer and Cyclization vol.32, pp.5, 2003, https://doi.org/10.5012/bkcs.2011.32.5.1773
  26. 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
  27. Asymmetric Mannich-type Reactions of Fluorinated Ketoesters with Binaphthyl-Modified Thiourea Catalysts vol.32, pp.4, 2003, https://doi.org/10.5012/bkcs.2011.32.4.1195
  28. Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives from diethyl 2-fluoromalonate ester vol.10, pp.None, 2014, https://doi.org/10.3762/bjoc.10.119
  29. Enantioselective Michael Addition of Malonates to Chalcone Derivatives Catalyzed by Dipeptide-derived Multifunctional Phosphonium Salts vol.81, pp.20, 2003, https://doi.org/10.1021/acs.joc.6b01752
  30. 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
  31. Enantioselective Michael Addition of Malonates to Enones vol.24, pp.None, 2020, https://doi.org/10.2174/1385272824666200316122221