Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Diastereoselective Reduction of Chiral 2-(1-Alkenoyl)- and 2-(1-Alkynoyl)-1,3-Oxathiane 3-Oxides Derived from (1R)-(+)-Camphor

  • Received : 2012.02.11
  • Accepted : 2012.04.02
  • Published : 2012.07.20
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References

  1. Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191. https://doi.org/10.1021/cr980379w
  2. Roberstson, J.; Unsworth, W. P.; Lamont, S. G. Tetrahedron 2010, 66, 2363. https://doi.org/10.1016/j.tet.2010.01.107
  3. Colombo, L.; Di Giacomo, M.; Brusotti, G.; Milano, E. Tetrahedron Lett. 1995, 36, 2863. https://doi.org/10.1016/0040-4039(95)00369-N
  4. Harder, T.; Lohl, T.; Bolte, M.; Wagner, K.; Hoppe, D. Tetrahedron Lett. 1994, 35, 7365. https://doi.org/10.1016/0040-4039(94)85315-0
  5. Eliel, E. L.; He, X.-C. J. Org. Chem. 1990, 55, 2114. https://doi.org/10.1021/jo00294a026
  6. Fukuzawa, S.; Miura, M.; Matsuzawa, H. Tetrahedron Lett. 2001, 42, 4167. https://doi.org/10.1016/S0040-4039(01)00676-1
  7. Uiterweerd, P. G. H.; van der Sluis, M.; Kaptein, B.; de Lange, B.; Kellogg, R. M.; Broxtermanb, Q. B. Tetrahedron: Asymmetry 2003, 14, 3479. https://doi.org/10.1016/j.tetasy.2003.08.040
  8. Ko, K.-Y.; Park, J.-Y. Tetrahedron Lett. 1997, 38, 407. https://doi.org/10.1016/S0040-4039(96)02311-8
  9. Ko, K.-Y.; Yun, H. Heterocycles 2010, 81, 2351. https://doi.org/10.3987/COM-10-12016
  10. Ko, K.-Y.; Frazee, W. J.; Eliel, E. L. Tetrahedron 1984, 40, 1333. https://doi.org/10.1016/S0040-4020(01)82419-4
  11. Chacon-García, L.; Lagunas-Rivera, S.; Perez-Estrada, S.; Vargas- Diaz, M. E.; Joseph-Nathan, P.; Tamariz, J.; Gerardo Zepeda, L. Tetrahedron Lett. 2004, 45, 2141. https://doi.org/10.1016/j.tetlet.2004.01.046
  12. Ko, K.-Y.; Kim, K.-I. Bull. Korean Chem. Soc. 1998, 19, 911.
  13. Bailey, W. F.; Reed, D. P.; Clark, D. R.; Kapur, G. N. Org. Lett. 2001, 3, 1865. https://doi.org/10.1021/ol015914k
  14. Ko, K.-Y.; Park, J.-Y. Bull. Korean Chem. Soc. 2002, 23, 665. https://doi.org/10.5012/bkcs.2002.23.5.665
  15. Solladie, G. In Advanced Asymmetric Synthesis; Stephenson, G. R., Ed.; Blackie: 1996.
  16. Page, P. C. B.; Prodger, J. C. Synlett. 1990, 460.
  17. Ko, K.-Y.; Kim, K.-I. Bull. Korean Chem. Soc. 1998, 19, 379.
  18. Herscovici, J.; Antonakis, K. J. Chem. Soc., Chem. Commun. 1980, 561.
  19. The enantiomeric excess of 6a was found to be ca. 96% by the proton NMR study of its 2-phenyl-1,3-dioxolanes doped with Eu(hfc)3. See: Eliel, E. L.; Ko, K.-Y. Tetrahedron Lett. 1983, 24, 3547. https://doi.org/10.1016/S0040-4039(00)88164-2
  20. Cossy, J. Synthesis 1987, 1113.
  21. Takano, S.; Iwabuchi, Y.; Ogasawara, K. Synlett. 1991, 548.
  22. Chun, J.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2003, 68, 348. https://doi.org/10.1021/jo026240+
  23. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977. https://doi.org/10.1021/cr010007e
  24. Ratier, M.; Castaing, M.; Godet, J. Y.; Pereyre, M. J. Chem. Res., Synop. 1978, 179.
  25. Charette, A. B.; Lebel, H. J. Org. Chem. 1995, 60, 2966. https://doi.org/10.1021/jo00115a008
  26. Mori, A.; Arai, I.; Yamamoto, H. Tetrahedron 1986, 42, 6447. https://doi.org/10.1016/S0040-4020(01)88107-2