Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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tert-Butyl 3-Oxo-4-(phenylsulfinyl)-2-(triphenyl-λ5-phosphanylidene)butanoate: A New Reagent for the Efficient Synthesis of Triphenylphosphorane Ylide Precursors to Vicinal Tricarbonyls from Alkyl Halides

  • Received : 2011.06.25
  • Accepted : 2011.07.15
  • Published : 2011.09.20
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Abstract

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References

  1. Rubin, M. B. Chem. Rev. 1975, 75, 177. https://doi.org/10.1021/cr60294a002
  2. Schoenberg, A.; Singer, E. Tetrahedron 1978, 34, 1285. https://doi.org/10.1016/0040-4020(78)88322-7
  3. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 5583. https://doi.org/10.1021/ja00170a024
  4. Findlay, J. A.; Liu, J.-S.; Burnell, D.; Nakashima, T. Can. J. Chem. 1982, 60, 2046. https://doi.org/10.1139/v82-289
  5. Toda, S.; Kotake, C.; Tsuno, T.; Narita, Y.; Yamasaki, T.; Konishi, M. J. Antibiot. 1992, 45, 1580. https://doi.org/10.7164/antibiotics.45.1580
  6. Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron 1997, 53, 59. https://doi.org/10.1016/S0040-4020(96)00978-7
  7. Wasserman, H. H.; Frechette, R.; Oida, T.; van Duzer, J. H. J. Org. Chem. 1989, 54, 6021.
  8. Wasserman, H. H.; Vu, C. B.; Cook, J. D. Tetrahedron 1992, 48, 2101. https://doi.org/10.1016/S0040-4020(01)88877-3
  9. Wasserman, H. H.; Hanke, S. L.; Luce, P.; Nakanishi, E.; Schulte, G. J. Org. Chem. 1990, 55, 5821. https://doi.org/10.1021/jo00310a012
  10. Wasserman, H. H.; Niu, C. BioMed. Chem. Lett. 1993, 3, 2437. https://doi.org/10.1016/S0960-894X(01)80972-0
  11. Wasserman, H. H.; Kuo, G.-H. Tetrahedron 1992, 48, 7071 https://doi.org/10.1016/S0040-4020(01)88248-X
  12. Schank, K.; Lick, C. Synthesis 1983, 392.
  13. Mahran, M. R.; Abdou, W. M.; Sidky, M. M.; Wamhoff, H. Synthesis 1987, 506.
  14. Detering, J.; Martin, H.-D. Angew. Chem., Int. Ed. Engl. 1988, 27, 695. https://doi.org/10.1002/anie.198806951
  15. Hoffman, R. V.; Wilson, A. L.; Kim, H.-O. J. Org. Chem. 1990, 55, 1267. https://doi.org/10.1021/jo00291a030
  16. Lindle, R. G.; Jeroncic, L. O.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 2534. https://doi.org/10.1021/jo00007a049
  17. Saba, A. Synth. Commun. 1994, 24, 695. https://doi.org/10.1080/00397919408012648
  18. Inokuchi, T.; Liu, P.; Torii, S. Chem. Lett. 1994, 1411
  19. Wasserman, H. H.; Ennis, D. S.; Blum, C. A.; Rotello, V. M. Tetrahedron Lett. 1992, 33, 6003. https://doi.org/10.1016/S0040-4039(00)61111-5
  20. Wasserman, H. H.; Baldino, C. M.; Coats, S. J. J. Org. Chem. 1995, 60, 8231. https://doi.org/10.1021/jo00130a023
  21. Wasserman, H. H.; Chen, J.-H.; Xia, M. J. Am. Chem. Soc. 1999, 122, 1401.
  22. Wasserman, H. H.; Amici, R. M. J. Org. Chem. 1989, 54, 5843. https://doi.org/10.1021/jo00286a007
  23. Wasserman, H. H.; Lee, K.; Xia, M. Tetrahedron Lett. 2000, 41, 2511. https://doi.org/10.1016/S0040-4039(00)00217-3
  24. Wasserman, H. H. Aldrich Acta 1987, 20, 63.
  25. Lee, K. Bull. Korean Chem. Soc. 2010, 31, 2776. https://doi.org/10.5012/bkcs.2010.31.10.2776
  26. Lee, K. Bull. Korean Chem. Soc. 2007, 28, 1641. https://doi.org/10.5012/bkcs.2007.28.10.1641
  27. Lee, K. Bull. Korean Chem. Soc. 2009, 30, 2521. https://doi.org/10.5012/bkcs.2009.30.11.2521
  28. Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. https://doi.org/10.1021/ja00801a058
  29. Herrmann, J. L.; Berger, M. H.; Schlessinger, R. H. J. Am. Chem. Soc. 1973, 95, 7923.
  30. Trost, B. M.; Leung, K. K. Tetrahedron Lett. 1975, 4197.
  31. Webb, K. S. Tetrahedron Lett. 1994, 35, 3457. https://doi.org/10.1016/S0040-4039(00)73209-6

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