Bulletin of the Korean Chemical Society

  • 제34권10호
  • /
  • Pages.2953-2958
  • /
  • 2013
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

A Versatile Synthesis of α-Keto (cyanomethylene)triphenylphosphorane Ylides from Alkyl Halides Utilizing a Noble Phenylsulfonyl Reagent

  • 투고 : 2013.05.22
  • 심사 : 2013.07.12
  • 발행 : 2013.10.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

A noble phenylsulfonyl reagent 8 having ${\alpha}$-oxo (cyanomethylene)triphenylphosphorane ylide subunit readily condensed with various alkyl halides under basic conditions to afford ${\beta}$-alkyl-${\alpha}$-oxo-${\beta}$-phenylsulfonyl (cyanomethylene)triphenylphosphorane ylides 9 in excellent yields. These sulfonyl ylides 9 were then reductively desulfonylated with $Na(Hg)/Na_2HPO_4$ in the presence of methanol to provide ${\alpha}$-keto (cyanomethylene)-triphenylphosphorane ylides 2' in good to excellent yields. Our new synthetic approach offers an expeditious access to various ${\alpha}$-keto (cyanomethylene)triphenylphosphorane ylides from alkyl halides utilizing a new phenylsulfonyl reagent as the key reagent under mild reaction conditions in good overall yields.

키워드

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. Wasserman, H. H.; Ho, W.-B. J. Org. Chem. 1994, 59, 4364. https://doi.org/10.1021/jo00095a005
  15. Wasserman, H. H.; Petersen, A. K. J. Org. Chem. 1997, 38,953.
  16. Wasserman, H. H.; Wang, J. J. Org. Chem. 1998, 63, 5581. https://doi.org/10.1021/jo980860m
  17. Wasserman, H. H.; Lee, K.; Xia, M. Tetrahedron Lett. 2000, 41, 2511. https://doi.org/10.1016/S0040-4039(00)00217-3
  18. Lee, K. Bull. Korean Chem. Soc. 2002, 23, 351. https://doi.org/10.5012/bkcs.2002.23.2.351
  19. 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
  20. Rodrigues, J. A. R.; Moran, P. J. S.; Milagre, C. D. F.; Ursini, C. V. Tetrahedron Lett. 2004, 45, 3579. https://doi.org/10.1016/j.tetlet.2004.03.062
  21. Seufert, W.; Fleury, A.; Giese, B. Synlett 2006, 1774.
  22. Price, W. S.; Fletcher, S.; Jorgensen, M. R.; Miller, A. D. Synlett 2006, 1933.
  23. Roche, S. P.; Faure, S.; El Blidi, L.; Aitken, D. J. Eur. J. Org. Chem. 2008, 30, 5067.
  24. Lee, K. Bull. Korean Chem. Soc. 2007, 28, 1641. https://doi.org/10.5012/bkcs.2007.28.10.1641
  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. 2009, 30, 2521. https://doi.org/10.5012/bkcs.2009.30.11.2521
  27. Najera, C.; Yus, M. Tetrahedron 1999, 55, 10547. https://doi.org/10.1016/S0040-4020(99)00600-6
  28. Weaver, J. D.; Tunge, J. A. Org. Lett. 2008, 10, 4657. https://doi.org/10.1021/ol801951e
  29. Zhang, T.; Huang, X.; Xue, J.; Sun, S. Tetrahedron Lett. 2009, 50, 1290. https://doi.org/10.1016/j.tetlet.2009.01.001
  30. Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Comprehensive Heterocyclic Chemistry II, Pergamon: Exeter, UK, 1996; Vol. 2, pp 207-968.
  31. Corey, E. J. Chaykovsky, M. J. Am. Chem. Soc. 1964, 86, 1639. https://doi.org/10.1021/ja01062a039
  32. Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477.
  33. Brown, A. C.; Carpino, L. A. J. Org. Chem. 1985, 50, 1749. https://doi.org/10.1021/jo00210a035
  34. Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 1135. https://doi.org/10.1021/jo00357a040
  35. Holton, R. A.; Crouse, D. A.; Williams, A. D.; Kennedy, R. M. J. Org. Chem. 1987, 52, 2317. https://doi.org/10.1021/jo00387a044
  36. Holmes, A. B.; Pooley, G. R. Tetrahedron 1992, 48, 7775. https://doi.org/10.1016/S0040-4020(01)80456-7
  37. Padwa, A.; Muller, C. L.; Rodriguez, A.; Watterson, S. H. Tetrahedron 1998, 54, 9651. https://doi.org/10.1016/S0040-4020(98)00522-5
  38. Streitwieser, A. Chem. Rev. 1956, 56, 571. https://doi.org/10.1021/cr50010a001
  39. Cox, D. J.; Fairbanks, A. J. Tetrahedron: Asymmetry 2009, 20, 773. https://doi.org/10.1016/j.tetasy.2009.02.018
  40. 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
  41. Wasserman, H. H.; Baldino, C. M.; Coats, S. J. J. Org. Chem. 1995, 60, 8231. https://doi.org/10.1021/jo00130a023
  42. Lee, K.; Im, J.-M. Bull. Korean Chem. Soc. 2000, 20, 1263.
  43. Wasserman, H. H.; Chen, J.-H.; Xia, M. Helv. Chim. Acta 2000, 83, 2607. https://doi.org/10.1002/1522-2675(20000906)83:9<2607::AID-HLCA2607>3.0.CO;2-B
  44. Lee, K.; Im, J.-M. Tetrahedron Lett. 2001, 42, 1539. https://doi.org/10.1016/S0040-4039(00)02280-2

피인용 문헌

  1. 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
  2. ChemInform Abstract: A Versatile Synthesis of α-Keto (Cyanomethylene)triphenylphosphorane Ylides from Alkyl Halides Utilizing a Noble Phenylsulfonyl Reagent. vol.45, pp.9, 2014, https://doi.org/10.1002/chin.201409198
  3. 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, 2013, https://doi.org/10.5012/bkcs.2013.34.12.3545