Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A New Synthesis of Triphenylphosphorane Ylide Precursors to α-Keto Amide/Ester and Tricarbonyl Units via Horner-Wadsworth-Emmons Reaction

  • Received : 2010.06.28
  • Accepted : 2010.08.05
  • Published : 2010.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Newly developed Horner-Wadsworth-Emmons (HWE) reagents 5 having triphenylphosphorane ylide subunits readily condensed with various carbonyl compounds under mild reaction conditions to afford $\beta,\gamma$-unsaturated $\alpha$-keto triphenylphorane ylides in good to excellent yields, which were hydrogenated over Pd-C (10%)/$H_2$ (1 atm) to give the corresponding $\alpha$-keto triphenylphorane ylides in quasi-quantitative yields. These triphenyphosphorane ylides have been utilized as the precursors to $\alpha$-keto amide/ester and vicinal tricarbonyl units in Wasserman's synthetic protocols, and have previously been prepared only from carboxylic acids/acid chlorides. Our new approaches provide excellent alternatives for the synthesis of triphenylphosphorane ylide precursors to $\alpha$-keto amide/ester and vicinal tricarbonyl units directly from carbonyl compounds in good to excellent yields.

Keywords

References

  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. Schoenberg, A.; Singer, E. Tetrahedron 1978, 34, 1285. https://doi.org/10.1016/0040-4020(78)88322-7
  4. Rubin, M. B. Chem. Rev. 1975, 75, 177. https://doi.org/10.1021/cr60294a002
  5. 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
  6. Findlay, J. A.; Liu, J.-S.; Burnell, D.; Nakashima, T. Can. J. Chem. 1982, 60, 2046. https://doi.org/10.1139/v82-289
  7. Fusetani, N.; Matsunaga, S.; Matsumoto, H.; Takebayashi, Y. J. Am. Chem. Soc. 1990, 112, 7053. https://doi.org/10.1021/ja00175a045
  8. 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
  9. Wasserman, H. H.; Kuo, G.-H. Tetrahedron 1992, 48, 7071. https://doi.org/10.1016/S0040-4020(01)88248-X
  10. Harbeson, S. L.; Abelleria, S. M.; Akiyama, A.; Barrett, R.; Carroll, R. M.; Straub, J. A.; Tkacz, J. N.; Wu, C.; Mosso, G. F. J. Med. Chem. 1994, 37, 2918. https://doi.org/10.1021/jm00044a013
  11. Harvey, A. J.; Abell, A. D. Tetrahedron 2000, 56, 9763. https://doi.org/10.1016/S0040-4020(00)00883-8
  12. Kokotos, G.; Kotsovolou, S.; Constantinou-Kokotou, V.; Beltzner, C. C.; Dennis, E. A. J. Med. Chem. 2002, 45, 2891. https://doi.org/10.1021/jm025538p
  13. Angelastro, M. R.; Peet, N. P.; Bey, P. J. Org. Chem. 1989, 54, 3913.
  14. Ocain, T. D.; Rich, D. H. J. Med. Chem. 1992, 35, 451. https://doi.org/10.1021/jm00081a005
  15. Wipf, P.; Kim, H-Y. J. Org. Chem. 1993, 58, 5592. https://doi.org/10.1021/jo00073a010
  16. Yang, Z.; Zhang, Z.; Meanwell, N. A.; Kadow, J. F.; Wang, T. Org. Lett. 2002, 7, 10245.
  17. Chen, J. J.; Deshpande, S. V. Tetrahedron Lett. 2003, 44, 8873. https://doi.org/10.1016/j.tetlet.2003.09.180
  18. 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
  19. Song, B.; Wang, S.; Sun, C.; Deng, H.; Xu, B. Tetrahedron Lett. 2007, 48, 8982. https://doi.org/10.1016/j.tetlet.2007.10.099
  20. Schank, K.; Lick, C. Synthesis 1983, 392.
  21. Detering, J.; Martin, H.-D. Angew. Chem., Int. Ed. Engl. 1988, 27, 695. https://doi.org/10.1002/anie.198806951
  22. Hoffman, R. V.; Wilson, A. L.; Kim, H.-O. J. Org. Chem. 1990, 55, 1267. https://doi.org/10.1021/jo00291a030
  23. Saba, A. Synth. Commun. 1994, 24, 695. https://doi.org/10.1080/00397919408012648
  24. Inokuchi, T.; Liu, P.; Torii, S. Chem. Lett. 1994, 1411.
  25. Wasserman, H. H.; Ho, W.-B. J. Org. Chem. 1994, 59, 4364. https://doi.org/10.1021/jo00095a005
  26. 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
  27. Wasserman, H. H.; Baldino, C. M.; Coats, S. J. J. Org. Chem. 1995, 60, 8231. https://doi.org/10.1021/jo00130a023
  28. Wasserman, H. H.; Chen, J.-H.; Xia, M. J. Am. Chem. Soc. 1999, 121, 1401. https://doi.org/10.1021/ja9840302
  29. Wasserman, H. H.; Lee, K.; Xia, M. Tetrahedron Lett. 2000, 41, 2511. https://doi.org/10.1016/S0040-4039(00)00217-3
  30. Wasserman, H. H.; Zhang, R. Tetrahedron 2002, 58, 6277. https://doi.org/10.1016/S0040-4020(02)00627-0
  31. Lee, K. Bull. Korean Chem. Soc. 2002, 23, 351. https://doi.org/10.5012/bkcs.2002.23.2.351
  32. Haberhauer, G. Synlett 2004, 1003.
  33. Price, W. S.; Fletcher, S.; Jorgensen, M. R.; Miller, A. D. Synlett 2006, 1933.
  34. Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87. https://doi.org/10.1021/cr60287a005
  35. Lee, K. Bull. Korean Chem. Soc. 2007, 28, 1641. https://doi.org/10.5012/bkcs.2007.28.10.1641
  36. Lee, K. Bull. Korean Chem. Soc. 2009, 30, 2521. https://doi.org/10.5012/bkcs.2009.30.11.2521
  37. Listvan, V. N.; Dombrovskii, A. V. Z. Obs. Khim. 1968, 38, 610.
  38. Liu, K.-G.; Yan, S.; Wu, Y.-L.; Yao, Z.-J. J. Org. Chem. 2002, 67, 6758. https://doi.org/10.1021/jo026056o
  39. Liu, K.-G.; Yan, S.; Wu, Y.-L.; Yao, Z.-J. Org. Lett. 2004, 6, 2269. https://doi.org/10.1021/ol0491890

Cited by

  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. ChemInform Abstract: A New Synthesis of Triphenylhosphorane Ylide Precursors to α-Keto Amide/Ester and Tricarbonyl Units via Horner-Wadsworth-Emmons Reaction. vol.42, pp.11, 2011, https://doi.org/10.1002/chin.201111198
  3. A New Synthesis of Phosphorane Ylide Precursors to Vicinal Tricarbonyls from Alkyl Halides Utilizing a Novel Phenylsulfonyl Reagent vol.59, pp.6, 2015, https://doi.org/10.5012/jkcs.2015.59.6.537
  4. Recent Developments in General Methodologies for the Synthesis of α-Ketoamides vol.116, pp.5, 2016, https://doi.org/10.1021/acs.chemrev.5b00443
  5. 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
  6. 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, 2010, https://doi.org/10.5012/bkcs.2013.34.12.3545