DOI QR코드

DOI QR Code

Diethyl [3-Cyano-2-Oxo-3-(Triphenylphosphoranylidene)propyl]phosphonate: A Useful Horner-Wadsworth-Emmons Reagent for α-Keto (Cyanomethylene)triphenylphosphoranes from Carbonyl Compounds

  • 발행 : 2007.10.20

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참고문헌

  1. Otto, H. H.; Schirmeister, T. Chem. Rev. 1997, 97, 133 https://doi.org/10.1021/cr950025u
  2. Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359 https://doi.org/10.1021/cr960370z
  3. Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Koto, T.; Hashimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 109, 5031 https://doi.org/10.1021/ja00250a050
  4. Schmodt, H.; Weinbrenner, S. J. Chem. Soc., Chem. Commun. 1994, 1003
  5. Han, W.; Hu, Z.; Jiang, X.; Wasserman, Z. R.; Decicco, C. R. Bioorg. Med. Chem. Lett. 2003, 13, 1111 https://doi.org/10.1016/S0960-894X(03)00031-3
  6. Tavares, F. X.; Deaton, D. A.; Miller, A. B.; Miller, L. R.; Wright, L. L.; Zhou, H.-Q. J. Med. Chem. 2004, 47, 5049 https://doi.org/10.1021/jm0400799
  7. Angelastro, M. R.; Peet, N. P.; Bey, P. J. Org. Chem. 1989, 54, 3913 https://doi.org/10.1021/jo00277a031
  8. Ocain, T. D.; Rich, D. H. J. Med. Chem. 1992, 35, 451 https://doi.org/10.1021/jm00081a005
  9. Wasserman, H. H.; Ho, W.-B. J. Org. Chem. 1994, 59, 4364 https://doi.org/10.1021/jo00095a005
  10. Kim, S.-K.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1827 https://doi.org/10.1016/S0040-4039(99)00079-9
  11. Yang, Z.; Zhang, Z.; Meanwell, N. A.; Kadow, J. F.; Wang, T. Org. Lett. 2002, 7, 10245
  12. Chen, J. J.; Deshpande, S. V. Tetrahedron Lett. 2003, 44, 8873 https://doi.org/10.1016/j.tetlet.2003.09.180
  13. Ma, M.; Li, C.; Peng, L.; Xie, F.; Zhang, X.; Wang, J. Tetrahedron Lett. 2005, 46, 3927 https://doi.org/10.1016/j.tetlet.2005.03.199
  14. Wong, M. K.; Yu, C.-W.; Yue, W.-H.; Yang, D. J. Org. Chem. 2001, 66, 3606 https://doi.org/10.1021/jo0015974
  15. Wasserman, H. H.; Chen, J.-H.; Xia, M. J. Am. Chem. Soc. 1999, 121, 1401 https://doi.org/10.1021/ja9840302
  16. Wasserman, H. H.; Zhang, R. Tetrahedron 2002, 58, 6277 https://doi.org/10.1016/S0040-4020(02)00627-0
  17. Haberhauer, G. Synlett 2004, 1003
  18. Price, W. S.; Fletcher, S.; Jorgensen, M. R.; Miller, A. D. Synlett 2006, 1933
  19. Wasserman, H. H.; Lee, K.; Xia, M. Tetrahedron Lett. 2000, 41, 2511 https://doi.org/10.1016/S0040-4039(00)00217-3
  20. Lee, K. Bull. Korean Chem. Soc. 2002, 23, 351 https://doi.org/10.5012/bkcs.2002.23.2.351
  21. Lee, K.; Kim, D.-K. J. Kor. Chem. Soc. 2004, 48, 161 https://doi.org/10.5012/jkcs.2004.48.2.161
  22. Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87 https://doi.org/10.1021/cr60287a005
  23. Listvan, V. N.; Dombrovskii, A. V. Z. Obs. Khim. 1968, 38, 610
  24. Liu, K.-G.; Yan, S.; Wu, Y.-L.; Yao, Z.-J. J. Org. Chem. 2002, 67, 6758 https://doi.org/10.1021/jo026056o
  25. Liu, K.-G.; Yan, S.; Wu, Y.-L.; Yao, Z.-J. Org. Lett. 2004, 6, 2269 https://doi.org/10.1021/ol0491890
  26. Lee, K.; Im, J.-M. Tetrahedron Lett. 2001, 42, 1539 https://doi.org/10.1016/S0040-4039(00)02280-2

피인용 문헌

  1. -phosphanylidene)butanoate: A New Reagent for the Efficient Synthesis of Triphenylphosphorane Ylide Precursors to Vicinal Tricarbonyls from Alkyl Halides vol.32, pp.9, 2011, https://doi.org/10.5012/bkcs.2011.32.9.3477
  2. Recent Developments in General Methodologies for the Synthesis of α-Ketoamides vol.116, pp.5, 2016, https://doi.org/10.1021/acs.chemrev.5b00443
  3. 3-Oxo-2-(triphenyl-λ5-phosphanylidene)-4-(phenylsulfinyl)butanenitrile:An Efficient Reagent for α-Keto (Cyanomethylene)triphenylphosphoranesfrom Alkyl Bromides vol.30, pp.11, 2007, https://doi.org/10.5012/bkcs.2009.30.11.2521
  4. 3-Oxo-2-(triphenyl-λ5-phosphanylidene)-4-(phenylsulfinyl)butanenitrile:An Efficient Reagent for α-Keto (Cyanomethylene)triphenylphosphoranesfrom Alkyl Bromides vol.30, pp.11, 2007, https://doi.org/10.5012/bkcs.2009.30.11.2521
  5. A New Synthesis of Triphenylphosphorane Ylide Precursors to α-Keto Amide/Ester and Tricarbonyl Units via Horner-Wadsworth-Emmons Reaction vol.31, pp.10, 2010, https://doi.org/10.5012/bkcs.2010.31.10.2776
  6. A Versatile Synthesis of α-Keto (cyanomethylene)triphenylphosphorane Ylides from Alkyl Halides Utilizing a Noble Phenylsulfonyl Reagent vol.34, pp.10, 2013, https://doi.org/10.5012/bkcs.2013.34.10.2953
  7. S-[3-Cyano-2-oxo-3-(triphenyl-λ5-phosphanylidene)propyl] O-ethyl Carbonodithioate: A Novel Xanthate Reagent for the Synthesis of α-keto (cyanomethylene)triphenylphosphorane Yli vol.34, pp.12, 2007, https://doi.org/10.5012/bkcs.2013.34.12.3545