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Enantioselective Michael Reaction of Fluoromalonates and Chalcones by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salt

  • Published : 2003.10.20

Abstract

Keywords

References

  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

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