DOI QR코드

DOI QR Code

BF3·OEt2-Mediated Ring Opening of Oxetanes with Ylides Derived from the Phosphoniosilylation Products of Enones

  • Jung, Sun-Ho (Department of Chemistry & Institute of Basic Science, Sungshin Women's University) ;
  • Jang, Sung-Yeun (Department of Chemistry & Institute of Basic Science, Sungshin Women's University)
  • Received : 2010.09.03
  • Accepted : 2010.09.10
  • Published : 2010.11.20

Abstract

Keywords

References

  1. Kozikowski, A. P.; Jung, S. H. J. Org. Chem. 1986, 51, 3400. https://doi.org/10.1021/jo00367a040
  2. Kozikowski, A. P.; Jung, S. H. Tetrahedron Lett. 1986, 27, 3227. https://doi.org/10.1016/S0040-4039(00)84760-7
  3. Kim, S.; Lee, P. H. Tetrahedron Lett. 1988, 29, 5413. https://doi.org/10.1016/S0040-4039(00)82882-8
  4. Kim, S.; Lee, P. H.; Kim, S. S. Bull. Korean Chem. Soc. 1989, 10, 218.
  5. Kim, S.; Kim, Y. G.; Park, J. H. Tetrahedron Lett. 1991, 32, 2043. https://doi.org/10.1016/S0040-4039(00)78903-9
  6. Kim, S.; Park, J. H.; Kim, Y. G.; Lee, J. M. J. Chem. Soc., Chem. Commun. 1993, 1188.
  7. Kim, S.; Lee, B. S.; Park, J. H. Bull. Korean Chem. Soc. 1993, 14, 654.
  8. Lee, P. H.; Kim, S. Bull. Korean Chem. Soc. 1992, 13, 580.
  9. Lee, P. H.; Cho, M.; Han, I.-S.; Kim, S. Tetrahedron Lett. 1999, 40, 6975. https://doi.org/10.1016/S0040-4039(99)01438-0
  10. Jung, S. H.; Kim, J. H. Bull. Korean Chem. Soc. 2002, 23, 365. https://doi.org/10.5012/bkcs.2002.23.3.365
  11. Jung, S. H.; Kim, J. H. Bull. Korean Chem. Soc. 2002, 23, 1375. https://doi.org/10.5012/bkcs.2002.23.10.1375
  12. Jung, S. H.; Kim, J. H.; Kim, H. J. Bull. Korean Chem. Soc. 2004, 25, 136. https://doi.org/10.5012/bkcs.2004.25.1.136
  13. Kim, J. H.; Jung, S. H. Bull. Korean Chem. Soc. 2004, 25, 1729. https://doi.org/10.5012/bkcs.2004.25.11.1729
  14. Kim, J. H.; Jung, S. H. Tetrahedron Lett. 2007, 48, 4243. https://doi.org/10.1016/j.tetlet.2007.04.067
  15. Shim, H. Y.; Jung, S. H. Bull. Korean Chem. Soc. 2008, 29, 2089. https://doi.org/10.5012/bkcs.2008.29.11.2089
  16. Ozouf, P.; Binot, G.; Pommelet, J.-C.; Lequeux, T. P. Org. Lett. 2004, 6, 3747. https://doi.org/10.1021/ol048549g
  17. Hickford, P. J.; Baker, J. R.; Bruce, I.; Booker-Miburn, K. I. Org. Lett. 2007, 9, 4681 https://doi.org/10.1021/ol701625q
  18. Isobe, H.; Fujino, T.; Yamazaki, N.; Guillat-Nieckowski, M.; Nakamura, E. Org. Lett. 2008, 10, 3729 https://doi.org/10.1021/ol801230k
  19. Bertolini, F.; Crotti, S.; Bussolo, V. D.; Macchia, F.; Pineschi, M. J. Org. Chem. 2008, 73, 8998. https://doi.org/10.1021/jo801568a
  20. Loy, R. N.; Jacobsen, E. N. J. Am. Chem. Soc. 2009, 131, 2786. https://doi.org/10.1021/ja809176m
  21. Christlieb, M.; Davies, J. E.; Eames, J.; Hooley, R.; Warren, S. J. Chem. Soc., Perkin Trans. 1 2001, 2983.

Cited by

  1. ChemInform Abstract: BF3·OEt2-Mediated Ring Opening of Oxetanes with Ylides Derived from the Phosphoniosilylation Products of Enones. vol.42, pp.13, 2011, https://doi.org/10.1002/chin.201113042
  2. A New Entry to β-Functionalization of Enones: Pentyloxy Group Incorporation in the TBSOTf-Mediated Ring-Opening Reaction of Epoxides with Ylides Derived from the Phosphoniosilylation Products of vol.35, pp.8, 2014, https://doi.org/10.5012/bkcs.2014.35.8.2573
  3. Ring-opening reactions of oxetanes: A review of methodology development and synthetic applications vol.46, pp.17, 2010, https://doi.org/10.1080/00397911.2016.1208245
  4. Divergent Reactivity via Cobalt Catalysis: An Epoxide Olefination vol.18, pp.3, 2010, https://doi.org/10.1021/acs.orglett.5b03514