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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

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