Synthesis and stereochemistry of optically active selenium and tellurium compounds

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 180, Issue 3-4, 2005, Pages 667-678

  Kamigata, Nobumasa ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

Absolute configuration; CD spectrum; Diphenyl dichalcogenide; Optical resolution; Optically active compound; Racemization; Seleninic acid; Specific rotation; Stereochemistry; Telluronium imide; Telluronium salts; X ray crystallographic analysis

Indexed keywords

EID: 27144547566     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426500590907345     Document Type: Conference Paper

References (59)

1. P. Metzner and A. Thuillier, Sulfur Reagents in Organic Synthesis (Academic Press, London, 1993).
2. The Chemistry of Sulphone and Sulphoxides (Eds.: S. Patai, A. Rappoport, and C. J. M. Stirling) (John Wiley & Sons, New York, 1981).
3. The Chemistry of the Sulphonium Group (Eds.: C. J. M. Stirlimg and S. Patai) (John Wiley & Sons, New York, 1981).
4. M. Mikolajczk and J. Drabowicz (Eds.: N. Allinger, E. L. Eliel, and S. H. Wilen), Top. Stereochem., John Wiley & Sons, New York, 13, 333 (1982).
5. The Chemistry of Organic Selenium and Tellurium Compounds (Eds.: S. Patai and Z. Rappoport) (John Wiley & Sons, New York, 1987).
6. Organoselenium Chemistry (Eds.: D. Liotta) (John Wiley & Sons, New York, 1987).
7. C. Paulmier, Selenium Reagents and Intermediate in Organic Synthesis (Pergamon Press, Oxford, 1986).
8. Organic Selenium Compounds: Their Chemistry and Biology (Eds.: D. L. Lkayman and W. H. H. Günther) (John Wiley & Sons, New York, 1973).
9. N. Kamigata and T. Shimizu, Rev. Heteroatom Chem., 4, 226 (1991).
10. T. Shimizu and N. Kamigata, Rev. Heteroatom Chem., 18, 11 (1998).
11. T. Shimizu and N.Kamigata, Org. Prep. Proced. Int., 29, 603 (1999).
12. F. A. Davis, J. M. Billmers, and O. D. Stringer, Tetrahedron Lett., 24, 3191 (1983).
13. T. G. Back, N. Ibrahim, and D. J. McPhee, J. Org. Chem., 47, 3283 (1982).
14. D. N. Jones, D. Mundy, and R. D. Whitehouse, J. Chem. Soc., Chem. Commun., 86 (1970).
15. N. Zylber, J. Zylber, and A. Gaudemer, J. Chem. Soc., Chem. Commun., 1084 (1978).
16. W. J. Pope and A. Nevillw, J. Chem. Soc., 1552 (1902).
17. F. G. Holliman and F. G. Mann, J. Chem. Soc., 1929 (1945).
18. F. G. Holliman and F. G. Mann, J. Chem. Soc., 1929 (1945).
19. T. M. Lowry and F. L. Gilbert, J. Chem. Soc., 2867 (1929).
20. V. P. Krasnov, V. I. Naddaka, and V. I. Minkin, Zh, Org. Khim, 17, 445 (1981).
21. F. A. Davis, J. M. Billmers, and O. D. Stringer, Tetrahedron Lett., 24, 3191 (1983).
22. F. A. Davis, O. D. Stringer, and J. P. McCauley, Jr., Tetrahedron Lett., 41, 4747 (1985).
23. K. Sasaki and S. Oae, Tetrahedron Lett., 3703 (1976).
24. T. Shimizu, M. Kobayashi, and N. Kamigata, Bull. Chem. Soc. Jpn., 61, 3761 (1988).
25. T. Shimizu, M. Kobayashi, and N. Kamigata, Sulfur Lett., 8, 61 (1988).
26. T. Shimizu, K. Kikuchi, Y. Ishikawa, I. Ikemoto, M. Kobayashi, and N. Kamigata, J. Chem. Soc., Perkin Trans., 1, 597 (1989).
27. T. Shimizu, M. Kobayashi, and N. Kamigata, Bull. Chem. Soc. Jpn., 62, 2099 (1989).
28. H. Fueno, S. Ikuta, H. Matsuyama, and N. Kamigata, J. Chem. Soc. Perkin Trans., 2, 1925 (1992).
29. T. Shimizu, M. Inomoto, H. Taka, and N. Kamigata, J. Org. Chem., 64, 8242 (1999).
30. H. Taka, A. Matsumoto, T. Shimizu, and N. Kamigata, Chem. Lett., 726 (2000).
31. T. Shimizu, Y. Yamazaki, H. Taka, and N. Kamigata, J. Am. Chem. Soc., 119, 5966 (1997).
32. T. Shimizu, Y. Yamazaki, H. Taka, and N. Kamigata, Phosphorus, Sulfur and Silicon, 136-138, 607 (1998).
33. H. Taka, Y. Yamazaki, T. Shimizu, and N. Kamigata, J. Org. Chem., 65, 2127 (2000).
34. H. Taka, A. Matsumoto, T. Shimizu, and N. Kamigata, Heteroatom Chem., 12, 227 (2001).
35. T. Shimizu, T. Urakubo, P. Jin, M. Kondo, S. Kitagawa, and N. Kamigata, J. Organomet. Chem., 539, 171 (1997).
36. N. Kamigata, H. Taka, A. Matsuhisa, H. Matsuyama, and T. Shimizu, Chem. Soc., Perkin Trans., 1, 2257 (1994).
37. N. Kamigata, H. Taka, A. Matsuhisa, and T. Shimizu, J. Phys. Org. Chem., 8, 139 (1995).
38. T. Shimizu, N. Seki, H. Taka, and N. Kamigata, J. Org. Chem., 61, 6013 (1996).
39. T. Shimizu, N. Kamigata, and S. Ikuta, J. Chem. Soc., Perkin Trans., 2, 1469 (1999).
40. H. Taka, T. Shimizu, F. Iwasaki, M. Yasui, and N. Kamigata, J. Org. Chem., 64, 7433 (1999).
41. M. Yasui, H. Taka, T. Shimizu, N. Kamigata, and F. Iwasaki, Acta Cryst., C55, 1861 (1999).
42. N. Kamigata, Y. Nakamura, H. Matsuyama, and T. Shimizu, Chem. Lett., 249 (1991).
43. N. Kamigata, Y. Nakamura, K. Kikuchi, I. Ikemoto, T. Shimizu, and H. Matsuyama, J. Chem. Soc., Perkin Trans., 1, 1721 (1992).
44. N. Kamigata, A. Matsuhisa, H. Taka, and T. Shimizu, J. Chem. Soc., Perkin Trans., 1, 821 (1995).
45. T. Shimizu, A. Matsuhisa, N. Kamigata, and S. Ikuta, J. Chem. Soc., Perkin Trans., 2, 1805 (1995).
46. T. Shimizu, T. Urakubo, and N. Kamigata, Chem. Lett., 297 (1996).
47. T. Shimizu, T. Urakubo, and N. Kamigata, J. Org. Chem., 61, 8032 (1996).
48. N. Kamigata, T. Urakubo, and T. Shimizu, Phosphorus, Sulfur and Silicon, 136-138, 493 (1998).
49. T. Shimizu, Y. Machida, and N. Kamigata, Eur. J. Org. Chem., 2265 (2002).
50. T. Shimizu, Y. Machida, and N. Kamigata, Heteroatom Chem., 14, 523 (2003).
51. T. Shimizu, I. Watanabe, and N. Kamigata, Angew. Chem., 113, 2526 (2001).
52. T. Shimizu, Y. Nakashima, I. Watanabe, K. Hirabayashi, and N. Kamigata, J. Chem. Soc., Perkin Trans., 1, 2151 (2002).
53. T. Shimizu, H. Isono, M. Yasui, F. Iwasaki, and N. Kamigata, Org. Lett., 3, 3639 (2001).
54. D. Darwish and C. E. Scott, Can. J. Chem., 51, 3647 (1973).
55. T. M. Lowry and F. L. Gilbert, J. Chem. Soc., 2867 (1929).
56. H. Taka, T. Shimizu, F. Iwasaki, M. Yasui, and N. Kamigata, J. Org. Chem., 64, 7433 (1999).
57. T. Shimizu, N. Kamigata, and S. Ikuta, J. Chem. Soc., Perkin Trans., 2, 1469 (1999).
58. L. Egartner, F. Halla, and R. Schacherl, Z. Phys. Chem. B, 18, 189 (1932).
59. P. G. Llabres, O. Dideberg, and L. Dupont, Act Crystallogr., B28, 2438 (1972).