Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Direct Utilization of Naturally Occurring Sulfides for the Asymmetric Epoxidation of Aldehydes Mediated by Catalytic Ylides

  • Zanardi, Jacques (Laboratoire de Chimie Moleculaire et Thio-organique (UMR CNRS 6507), ENSICAEN-Universite de Caen) ;
  • Reboul, Vincent (Laboratoire de Chimie Moleculaire et Thio-organique (UMR CNRS 6507), ENSICAEN-Universite de Caen) ;
  • Metzner, Patrick (Laboratoire de Chimie Moleculaire et Thio-organique (UMR CNRS 6507), ENSICAEN-Universite de Caen)
  • Published : 2004.11.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Collins, A. N.; Sheldrake, G. N.; Crosby, J. Chirality in Industry II - Developments in the Commercial Manufacture and Applications of Optically Active Compounds; Wiley: Chichester, 1997.
  2. Tye, H.; Comina, P. J. J. Chem. Soc., Perkin Trans. 1 2001, 1729-1747.
  3. Blaser, H.-U. Chem. Commun. 2003, 293-296.
  4. Breuer, M.; Ditrich, K.; Habicher, T.; Hauer, B.; Kesseler, M.; Sturmer, R.; Zelinski, T. Angew. Chem. Int. Ed. 2004, 43, 788-824. https://doi.org/10.1002/anie.200300599
  5. Blaser, H. U.; Schmidt, E. Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions; Wiley-VCH: Weinheim, 2004.
  6. Dalko, P. I.; Moisan, L. Angew. Chem. Int. Ed. 2001, 40, 3726-3748. https://doi.org/10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO;2-D
  7. Herrmann, R. Stereoselective Synthesis (Houben-Weyl); Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Georg Thieme: Stuttgart, 1996; Vol. E21, pp 5759-6001.
  8. Blaser, H.-U. Chem. Rev. 1992, 92, 935-952. https://doi.org/10.1021/cr00013a009
  9. Kotha, S. Tetrahedron 1994, 50, 3639-3662. https://doi.org/10.1016/S0040-4020(01)90388-6
  10. Sheldon, R. A. Chirotechnology (Industrial Synthesis of Optically Active Compounds); Marcel Dekker: New York, 1993; pp 143-171.
  11. Sugimura, T.; Nakagawa, S.; Tai, A. Bull. Chem. Soc. Jpn 2002, 75, 355-363. https://doi.org/10.1246/bcsj.75.355
  12. Wynberg, H. Top. Stereochem. 1986, 16, 87-129. https://doi.org/10.1002/9780470147252.ch2
  13. Hermann, K.; Wynberg, H. J. Org. Chem. 1979, 44, 2238-2244. https://doi.org/10.1021/jo01327a043
  14. Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417-430. https://doi.org/10.1021/ja00392a029
  15. Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166-168. https://doi.org/10.1021/ja00365a030
  16. Kazmaier, U.; Krebs, A. Angew. Chem. Int. Ed. 1998, 34, 2012-2014.
  17. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 87-129.
  18. Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372. https://doi.org/10.1021/cr960411r
  19. Aggarwal, V. K.; Richardson, J. Chem. Commun. 2003, 2644-2651.
  20. Julienne, K.; Metzner, P.; Henryon, V.; Greiner, A. J. Org. Chem. 1998, 63, 4532-4534. https://doi.org/10.1021/jo980269p
  21. Julienne, K.; Metzner, P.; Henryon, V. J. Chem. Soc., Perkin Trans. 1 1999, 731-736.
  22. Zanardi, J.; Leriverend, C.; Aubert, D.; Julienne, K.; Metzner, P. J. Org. Chem. 2001, 66, 5620-5623. https://doi.org/10.1021/jo015588m
  23. Lieser, J. K. Synth. Commun. 1983, 13, 765-767. https://doi.org/10.1080/00397918308063707
  24. Haberland, J.; Hummel, W.; Daussmann, T.; Liese, A. Org. Proc. Res. Dev. 2002, sous presse.
  25. Aggarwal, V. K.; Alonso, E.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Porcelloni, M.; Studley, J. R. Angew. Chem. Int. Ed. 2001, 40, 1430-1433. https://doi.org/10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO;2-W
  26. Saito, T.; Akiba, D.; Sakairi, M.; Kanazawa, S. Tetrahedron Lett. 2001, 42, 57-59. https://doi.org/10.1016/S0040-4039(00)01878-5
  27. Li, A.-H.; Dai, L.-X.; Hou, X.-L.; Huang, Y.-Z.; Li, F.-W. J. Org. Chem. 1996, 61, 489-493. https://doi.org/10.1021/jo951442+
  28. Solladie-Cavallo, A.; Diep-Vohuule, A. J. Org. Chem. 1995, 60, 3494-3498. https://doi.org/10.1021/jo00116a041
  29. Winn, C. L.; Bellenie, B. R.; Goodman, J. M. Tetrahedron Lett. 2002, 43, 5427-5430. https://doi.org/10.1016/S0040-4039(02)01072-9
  30. Ishizaki, M.; Hoshino, O. Heterocycles 2002, 57, 1399-1402. https://doi.org/10.3987/COM-02-9520
  31. Hayakawa, R.; Shimizu, M. Synlett 1999, 1328-1330.
  32. Miyake, Y.; Oyamada, A.; Nishibayashi, Y.; Uemura, S. Heteroatom Chem. 2002, 13, 270-275. https://doi.org/10.1002/hc.10028
  33. Myllymaki, V. T.; Lindvall, M. K.; Koskinen, A. M. P. Tetrahedron 2001, 57, 4629-4635. https://doi.org/10.1016/S0040-4020(01)00396-9
  34. Bell, M. R.; Carlson, J. A.; Oesterlin, R. J. Org. Chem. 1972, 37, 2733-2735. https://doi.org/10.1021/jo00982a023
  35. Denerley, P. M.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1979, 3175-3189. https://doi.org/10.1039/p19790003175
  36. De Clercq, P. J. Chem. Rev. 1997, 97, 1755-1792. https://doi.org/10.1021/cr950073e
  37. Aggarwal, V. K. Synlett 1998, 329-336.
  38. Aggarwal, V. K. Comprehensive Asymmetric Catalysis; Jacobsen, E.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, pp 679-693.
  39. Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, in the press.
  40. Solladie-Cavallo, A.; Diep-Vohuule, A.; Sunjic, V.; Vinkovic, V. Tetrahedron: Asymmetry 1996, 7, 1783-1788. https://doi.org/10.1016/0957-4166(96)00213-3
  41. Miniere, S.; Reboul, V.; Arrayas, R. G.; Metzner, P.; Carretero, J. C. Synthesis 2003, 2249-2254.
  42. Aggarwal, V. K.; Calamai, S.; Ford, G. J. J. Chem. Soc., Perkin Trans. 1 1997, 593-599.
  43. Aggarwal, V. K.; Harvey, J. N.; Richardson, J. J. Am. Chem. Soc. 2002, 124, 5747-5756. https://doi.org/10.1021/ja025633n

Cited by

  1. Direct Utilization of Naturally Occurring Sulfides for the Asymmetric Epoxidation of Aldehydes Mediated by Catalytic Ylides. vol.36, pp.13, 2005, https://doi.org/10.1002/chin.200513107