Optically pure chalcogenuranes: Synthesis and stereochemistry of their reactions

Phosphorus, Sulfur and Silicon and Related Elements

Volumn 157, Issue , 2000, Pages 225-252

  Zhang, Jian ^a,b   Koizumi, Toru ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034338704     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426500008040525     Document Type: Article

References (93)

1. Reviews on the reactions of the pentacoordinated silicon and phosphorus compounds: (a) R. R. Holmes, Acc. Chem. Res., 5, 296 (1972).
2. (b) R. R. Holmes, Acc. Chem. Res., 12, 257 (1979).
3. C. Chuit, R. J. P. Corriu, C. Reye and J. C. Young, Chem. Rev., 93, 1371 (1993).
4. K. B. Dillon, Chem. Rev., 94, 1441 (1994).
5. R. R. Holmes, Chem. Rev., 96, 927 (1996). Recent examples:
6. (f) N. Y. Chang and C. Lim, J. Am. Chem. Soc., 120, 2156 (1998).
7. (g) K. Kubo, H. Nakazawa, K. Kawamura, T. Mizuta and K. Miyoshi, J. Am. Chem. Soc., 120, 6715 (1998).
8. Reviews on the chemistry of chalcogenuranes: (a) J. C. Martin and I. C. Paul, Science, 191, 154 (1976).
9. (b) J. C. Martin, Science, 221, 509 (1983).
10. R. A. Hayes and J. C. Martin, in Organic Sulfur Chemistry, Theoretical and Experimental Advances, (F. Bernardi, I. G. Csizmadia and A. Mangini, Eds. Elsevier, Amsterdam, 1985), pp. 408-483,
11. S. Oae, Organic Sulfur Chemistry: Structure and Mechanism, (CRC Press, Boca Raton, FL, 1991).
12. (a) E. J. Corey and X. M. Cheng, The Logic of Chemical Synthesis, (John Wiley & Sons, 1989).
13. (b) D. Seebach, Angew. Chem. Int. Ed. Engl., 29, 320 (1990).
14. K. C. Nicolaou and E. J. Sorense, Classics in Total Synthesis, (VCH Publisher, Inc. New York, 1996).
15. R. Noyori and S. Hashiguchi, Acc. Chem. Res., 30, 97 (1997).
16. (e) V. Fehring and R. Selke, Angew. Chem. Int. Ed. Engl., 37, 1827 (1998). Some excellent examples:
17. (f) K. Soai, T. Shibata, H. Morioka and K. Choji, Nature, 378, 767 (1995).
18. (g) A. E. Rubin and K. B. Sharpless, Angew. Chem. Int. Ed. Engl., 36, 2637 (1997).
19. (h) K. Mikami and M. Shimizu, Nature, 385, 613 (1997).
20. M. Tokunaka, J. F. Larrow, F. Kakiuchi and E. N. Jacobsen, Science, 277, 936 (1997).
21. (j) T. Shibata, J. Yamamoto, N. Mastumoto, S. Yonekubo, S. Osanai and K. Soai, J. Am. Chem. Soc., 20, 12157 (1998).
22. (a) T. Shimizu and N. Kamigata, Org. Prep. Proced. Int., 29, 605 (1997).
23. (b) T. Shimizu and N. Kamigata, J. Synth. Org. Chem. Jpn., 55, 35 (1997).
24. (a) A. J. Mancuso and D. Swern, Synthesis, 165 (1981).
25. (b) T. T. Tidwell, Synthesis, 857 (1990).
26. Y. Kita, Phosphorus, Sulfur and Silicon, 120 & 121, 145 (1997).
27. S. Oae and Y. Uchida, Acc. Chem. Res., 24, 202 (1991).
28. T. Kawashima and R. Okazaki, Synlett, 600 (1996).
29. (a) K. L. House, R. B. Dunlap, J. D. Odor, Z.-P. Wu and D. Hilvert, J. Am. Chem. Soc., 114, 8573 (1992).
30. (b) L. Engman, D. Stern, I. A. Cotgreave and C. M. Andersson, J. Am. Chem. Soc., 114, 9737 (1992).
31. L. Engman, D. Stern, M. Pelcman and C. M. Andersson, J. Org. Chem., 59, 1973 (1994).
32. M. R. Detty, A. E. Friedman and A. R. Oseroff, J. Org. Chem., 59, 8245 (1994).
33. (e) M. Iwaoka and S. Tomoda, J. Am. Chem. Soc., 116, 2557 (1994).
34. (f) K. Vessman, M. Ekslröm, M. Berglund, C. M. Andersson and L. Engman, J. Org. Chem., 60, 4461 (1995).
35. (g) A. Mohsine and L. Christiaens, Heterocycles, 43, 2567 (1996).
36. (h) T. G. Back and B. P. Dyck, J. Am. Chem. Soc., 119, 2079 (1997).
37. M. C. Fong and C. H. Schiesser, J. Org. Chem., 62, 3103 1997).
38. (j) M. R. Detty, F. Zhou and A. E. Friedman, J. Am. Chem. Soc., 118, 313 (1996).
39. (k) A. Albeck, H. Weitman, B. Sredni and M. Albeck, Inorg. Chem., 37, 1704 (1998).
40. (a) Y. N. Yamakoshi, W. Y. Ge, K. Okayama, T. Takahashi and T. Koizumi, Heterocycles. 42, 129 (1996).
41. (b) K. Nishide, Y. Shigeta, K. Obata and M. Node, J. Am. Chem. Soc., 118, 13103 (1996).
42. V. K. Aggarwal, J. G. Ford, S. Fonquerna, H. Adams, R. V. H. Jones and R. Fieldhouse, J. Am. Chem. Soc., 120, 8328 (1998).
43. M. C. Aversa, A. Barattucci, P. Bonaccorsi, P. Giannetto, M. Panzalorto and S. Rizzo, Tetrahedron: Asymmetry, 9, 1577 (1998), and references cited therein.
44. (a) T. M. Balthazor and J. C. Martin, J. Am. Chem. Soc., 97, 5634 (1975).
45. (b) J. C. Martin and T. M. Balthazor, J. Am. Chem. Soc., 99, 152 (1977).
46. M. Moriyama, T. Yoshimura, N. Furukawa, T. Numata and S. Oae, Tetrahedron, 32, 3003 (1976).
47. M. Matsugi, K. Hashimoto, M. Inai, N. Fukuda, T. Furuta, J. Minamikawa and S. Otsuka, Tetrahedron: Asymmetry, 6, 2991 (1995).
48. (e) K. Hashimoto, M. Matsugi, N. Fukuda and Y. Kurogi, Phosphorus, Sulfur and Silicon, 120 & 121, 305 (1997).
49. J. Zhang, T. Takahashi and T. Koizumi, Heterocycles, 44, 325 (1997).
50. (a) T. Takahashi, N. Kurose, S. Kawanami, Y. Arai, T. Koizumi and M. Shiro, J. Org. Chem., 59, 3262 (1994).
51. (b) N. Kurose, T. Takahashi and T. Koizumi, Tetrahedron, 53, 12115 (1997).
52. (a) T. Takahashi, J. Zhang, N. Kurose, S. Takahashi, T. Koizumi and M. Shiro, Tetrahedron: Asymmetry: 7, 2797 (1996).
53. (b) J. Zhang, S. Saito and T. Koizumi, J. Org. Chem., 63, 5423 (1998).
54. B. Lindgren, Acta. Chem. Scand., 26, 2560 (1972).
55. P. Huszthy, I. Kapovits, Á. Kucsman and L. Radics, Tetrahedron Lett., 1853 (1978).
56. S. Allenmark and S. Claeson, Tetrahedron: Asymmetry, 4, 2329 (1993).
57. (a) J. Drabowicz and J. C. Martin, Tetrahedron: Asymmetry, 4, 297 (1993).
58. (b) J. Drabowicz and J. C. Martin, Pure & Appl. Chem., 68, 951 (1996).
59. D. Szabó, S. Szendeffy, I. Kapovits, Á. Kucsman, M. Czugler, A. Kálmán and P. Nagy, Tetrahedron: Asymmetry: 8, 2411 (1997).
60. (a) J. Zhang, S. Saito and T. Koizumi, J. Am. Chem. Soc., 120, 1631 (1998).
61. (b) J. Zhang, S. Saito and T. Koizumi, J. Org. Chem., 63, 9375 (1998).
62. J. Zhang, S. Takahashi, S. Saito and T. Koizumi, Tetrahedron: Asymmetry, 9, 3303 (1998).
63. (a) L. J. Adzima and J. C. Martin, J. Org. Chem., 42, 4006 (1977).
64. (b) I. Kapovits, J. Rábai, D. Szabó, K. Czakó, A. Kucsman, G. Argay, V. Fülöp, A. Kálmán, T. Koritsánszky and L. Párkányi, J. Chem. Soc., Perkin Trans. 2, 847 (1993).
65. S. F. Hornbuckle, P. Livant and T. R. Webb, J. Org. Chem., 60, 4153 (1995).
66. D. Szabó, I. Kapovits, G. Argay, M. Czugler, A. Kálmán and T. Koritsánszky, J. Chem. Soc., Perkin Trans. 2, 1045 (1997).
67. J. Zhang, S. Saito and T. Koizumi, Tetrahedron: Asymmetry, 8, 3357 (1997).
68. J. Zhang, S. Saito and T. Koizumi, J. Org. Chem., 63, 5265 (1998).
69. H. Takada, M. Oda, Y. Miyake, K. Ohe and S. Uemura, Chem. Commun., 1557 (1998).
70. T. Takahashi, N. Kurose, S. Kawanami, A. Nojiro, Y. Arai, T. Koizumi and M. Shiro, Chem. Lett., 379 (1995).
71. S. Saito, J. Zhang and T. Koizumi, J. Org. Chem., 63, 6029 (1998).
72. S. Takahashi, J. Zhang, S. Saito and T. Koizumi, Heterocycles, 46, 373 (1997).
73. J. Zhang, Ph. D. Thesis, Toyama Medical & Pharmaceutical University (1998).
74. Recent review on the telluronium salts: (a) Y. Z Huang, Y. Tang and Z. L. Zhou, Tetrahedron, 54, 1667 (1998). Recent review on the optically active ylides:
75. (b) A. H. Li, L. X. Dai and V. K. Aggarwal, Chem. Rev., 97, 2341 (1997).
76. (a) T. M. Lowry and F. L. Gilbert, J. Chem. Soc., 2867 (1929).
77. (b) F. G. Holliman and F. G. Mann, J. Chem. Soc., 37 (1945).
78. T. Shimizu, T. Urakubo and N. Kamigata, Chem. Lett., 297 (1996).
79. T. Shimizu, T. Urakubo and N. Kamigata, J. Org. Chem., 61, 8032 (1996).
80. (a) E. Vass, F. Ruff, I. Kapovits, J. Rábai and D. Szabó, J. Chem. Soc., Perkin Trans. 2, 855 (1993).
81. (b) E. Vass, F. Ruff, I. Kapovits, D. Szabó and Á. Kucsman, J. Chem. Soc., Perkin Trans. 2, 2061 (1997).
82. T. Ádám, F. Ruff, I. Kapovits, D. Szabó and Á. Kucsman, J. Chem. Soc., Perkin Trans. 2, 1269 (1998).
83. (a) J. N. Fitzner, R. G. Shea, J. E. Fankhauser and P. B. Hopkins, J. Org. Chem., 50, 417 (1985).
84. (b) H. J. Reich and K. E. Yelm, J. Org. Chem., 56, 5672 (1991).
85. F. A. Davis and T. Reddy, J. Org. Chem., 57, 2599 (1992).
86. K. Komatsu, Y. Nishibayashi and S. Uemura, Tetrahedron Lett., 34, 2449 (1993).
87. (e) Y. Nishibayashi, J. D. Singh, S. Fukuzawa and S. Uemura, J. Org. Chem., 60, 4114 (1995).
88. (f) Y. Nishibayashi, T. Chiba, K. Ohe and S. Uemura, J. Chem. Soc., Chem. Commun., 1243 (1995).
89. (g) Y. Nishibayashi, K. Ohe and S. Uemura, J. Chem. Soc., Chem. Commun., 1245 (1995).
90. N. Kurose, T. Takahashi and T. Koizumi, J. Org. Chem., 61, 2932 (1996).
91. N. Kurose, T. Takahashi and T. Koizumi, J. Org. Chem., 62, 4562 (1997).
92. (a) T. Takahashi, N. Nakao and T. Koizumi, Chem. Lett., 207 (1996).
93. (b) T. Takahashi, N. Nakao and T. Koizumi, Tetrahedron: Asymmetry, 8, 3293 (1997).