Fragmentation and cleavage reactions mediated by smi2. Part 1: X-y, x-x and c-c substrates

Organic Preparations and Procedures International

Volumn 33, Issue 6, 2001, Pages 565-602

  Williams, D Bradley G ^a   Blann, Kevin ^a   Caddy, Judy ^a  

^a UNIVERSITY OF JOHANNESBURG   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

CLEAVAGE REACTION; FRAGMENTATION REACTIONS;

SAMARIUM COMPOUNDS;

EID: 0035649760     PISSN: 00304948     EISSN: 19455453     Source Type: Journal    
DOI: 10.1080/00304940109356621     Document Type: Article

References (110)

1. P. Girard, J. L. Namy and H. B. Kagan, J. Am. Chem. Soc., 102,2693 (1980).
2. C. A. Cooley and D. M. Yost, Inorg. Synth., 2, 69 (1946);
3. D. A. Johnson, Aî/v. Inorg. Radiochem., 20, 1 (1970).
4. G. A. Molander, Chem. Rev., 92, 29 (1992).
5. D. A. Johnson, J. Chem. Soc. Dalton Trans. 1671 (1974);
6. L. R. Morss, Chem. Rev., 76, 827(1976).
7. M. Shabangi and R. A. Flowers, II, Tetrahedron Lett., 38, 1137 (1997);
8. R. J. Enemærke, K. Daasbjerg and T. Skrydstrup, Chem. Commun., 343 (1999);
9. J. Inanaga, M. Ishikawa and M. Yamaguchi, Chem. Lett., 1485 (1987).
10. D. P. Curran, T. L. Fevig, C. P. Jasperse and M. J. Totleben, Synlett., 943 (1992).
11. H. B. Kagan and J. L. Namy, Tetrahedron, 42, 6573 (1986).
12. D. P. Curran and M.J. Totleben, J. Am. Chem. Soc., 114, 6050 (1992).
13. M. Matsukuwa, J. Inanaga, and M. Yamaguchi, Tetrahedron Lett., 28, 5877 (1986);
14. T. L. Fevig, R. L. Elüott and D. P. Curran, J. Am. Chem. Soc., 110, 5064 (1988).
15. E. J. Enholm and A. Travellas, J. Am. Chem. Soc., 111, 6463 (1989).
16. H. M. R. Hoffmann, I. Münnich, O. Nowitzki, H. Stucke and D. J. Williams, Tetrahedron, 52, 11783 (1996);
17. O. Nowitzki, I. Münnich, H. Stucke, and H. M. R. Hoffmann, Tetrahedron, 52, 11799 (1996).
18. E. Hasegawa and D. P. Curran, J. Org. Chem., 58, 5008 (1993).
19. M. Shabangu, J. M. Sealy, J. R. Fuchs, and R. A. Flowers, II, Tetrahedron Lett., 39,4429 (1998).
20. Y. Handa, J. Inanaga, and M. Yamaguchi, J. Chem. Soc., Chem. Commun., 298 (1989);
21. A. S. Kende, and J. S. Mendoza, Tetrahedron Lett., 32, 1699 (1991).
22. N. R. Natale, Tetrahedron Lett., 23, 5009 (1982).
23. Y. Zhang and R. Lin, Synth. Commun., 17, 329 (1987).
24. G. E. Keck, S. F. McHardy and J. A. Murry, J. Am. Chem. Soc., 117, 7289 (1995);
25. E. Keck, S. F. McHardy, and T. T. Wäger, Tetrahedron Lett., 41, 7419 (1995);
26. G. E. Keck, S. F. McHardy and T. T. Wäger, Tetrahedron, 55, 11755 (1999).
27. S. E. Denmark, A. Stolle, J. A. Dixon and V. Guagnano, J. Am. Chem. Soc., 117, 2100 (1995);
28. S. S. Nikam, B. E. Komberg, D. R. Johnson and A. M. Doherty, Tetrahedron Lett., 36, 197 (1995);
29. A. R. Ritter, M. J. Miller, J. Org. Chem., 59, 4602 (1994);
30. R. C. Larock, “Comprehensive Organic Transformations”, p. 385, VCH Publishers Inc., New York, 1989.
31. J. Marco-Contelles, C. Destabel, J. L. Chiara and M. Bernabé, Tetrahedron:Asymmetry, 6, 1547 (1995);
32. J. L. Chiara, C. Destabel, P. Gallego and J. Marco- Contelles, J. Org. Chem., 61, 359 (1996).
33. B. J. McAuley, M. Nieuwenhuyzen and G. N. Sheldrake, Org. Lett., 2, 1457 (2000).
34. D. C. Hill, L. A. Flügge and P. A. Petillo, J. Org. Chem., 62, 4864 (1997);
35. E. Vedejs, and S. Lin, J. Org. Chem., 59, 1602 (1994);
36. A. Batch and R. H. Dodd, J. Org. Chem., 63, 872(1998).
37. C. Goulaouic-Dubois, A. Guggisberg and M. Hesse, J. Org. Chem., 60, 5969 (1995);
38. S. Knowles, A. F. Parsons, R. M. Pettifer and S. Rickling, Tetrahedron, 56,979;
39. H. Knowles, A. F. Parsons and R. M. Pettifer, Synlett., 271 (1997).
40. X. Jia, Y. Zhang and X. Zhou, Tetrahedron Lett., 35, 8833 (1994).
41. M. Kunishima, K. Hioki, T. Ohara, and S. Tani, J. Chem. Soc., Chem. Commun., 219 (1992)
42. C. R. Johnson and C. H. Senayake, J. Org. Chem., 54, 736 (1989).
43. K. S. Feldman and R. E. Simpson, Tetrahedron Lett., 30, 6985 (1989).
44. M. J. Burk and J. E. Feaster, J. Am. Chem. Soc., 114, 6266 (1992).
45. J. Souppe, L. Danon, J. L. Namy and H. B. Kagan, J. Organomet. Chem., 250, 227 (1983).
46. C. F. Sturino and A. G. Fallís, J. Am. Chem. Soc., 116, 7447 (1994).
47. R. S. Atkinson, B. J. Kelly and J. Williams, J. Chem. Soc., Chem. Commun., 373 (1992);
48. R. S. Atkinson, B. J. Kelly and J. Williams, Tetrahedron, 48, 7713 (1992).
49. X. Jia, Y. Zhang and X. Zhou, Synth. Commun., 24, 387 (1994).
50. X. Jia, Y. Zhang and X. Zhou, Synth. Commun., 24, 2898 (1994).
51. X. Jia, Y. Zhang and X. Zhou, Synth. Commun., 24, 1339 (1994);
52. X. Jia, Y. Zhang and X. Zhou, Synth. Commun., 25, 1913 (1995).
53. X. Jia, Y. Zhang and X. Zhou, Synth. Commun., 23, 189 (1993).
54. S. Zhang and Y. Zhang, J. Chem. Res. (S), 48 (1998).
55. S. Zhang and Y. Zhang, J. Chem. Res. (S), 350 (1998);
56. S. Zhang and Y. Zhang, Synth. Commun., 28, 3999 (1998).
57. T. P. Ananthanarayan, T. Gallagher and P. Magnus, J. Chem. Soc., Chem. Commun., 709 (1982).
58. T. Honda, K. Naito, S.-i. Yamane and Y. Suzuki, J. Chem. Soc., Chem. Commun., 1218 (1992).
59. G. A. Molander and J. A. McKie, J. Org. Chem., 56,4112 (1991).
60. T. Honda, S.-I. Yamane, K. Naito and Y. Suzuki, Heterocycles, 37, 515 (1994);
61. T. Honda, F. Ishikawa and S-i. Yamane, J. Chem. Soc., Chem. Commun., 499 (1994);
62. T. Honda, S-i. Yamane, K. Naito and Y. Suzuki, Heterocycles, 40, 301 (1995);
63. T. Honda, F. Ishikawa and S-i. Yamane, J. Chem. Soc., Perkin Trans. 1, 1125 (1996);
64. T. Honda, S-i. Yamane, F. Ishikawa and M. Katoh, Tetrahedron, 52, 12177 (1996);
65. T. Honda, M. Katoh and S-i. Yamane, J. Chem. Soc., Perkin Trans. 1, 2291 (1996).
66. T. Honda and F. Ishikawa, J. Org. Chem., 64, 5542 (1999).
67. G. A. Molander, J. B. Etter and P. W. Zinke, J. Am. Chem. Soc., 109,453 (1987).
68. H-Y. Kang and W. Sang Hong, Tetrahedron Lett., 42, 7661 (1995).
69. Q. Meng and M. Hesse, “Topics in Current Chemistry”, Vol. 161,107, Springer-Verlag, 1992.
70. C. Goulaouic-Dubois, A. Guggisberg, and M. Hesse, Tetrahedron, 51, 12035 (1995)
71. G. L. Lange and C. Gottardo, Tetrahedron Lett., 35, 6607 (1994).
72. G. L. Lange, C. Gottardo and A. Merica, J. Org. Chem., 64, 6738 (1999).
73. G. L. Lange and A. Merica, Tetrahedron Lett., 40, 7897 (1999).
74. G. L. Lange, L. Furlan and M.C. MacKinnon, Tetrahedron Lett., 39, 5489 (1998).
75. D. L. Comins and X. Zheng, J. Chem. Soc., Chem. Commun., 2681 (1994).
76. R. A. Batey and W. B. Motherwell, Tetrahedron Lett., 32, 6211 (1991);
77. R. A. Batey, J. D. Hading and W. B. Motherwell, Tetrahedron, 52, 11421 (1996).
78. G. A. Molander and C. Alonso-Alija, Tetrahedron, 53, 8067 (1997).
79. J.-T Hwang and C.-C Liao, Tetrahedron Lett., 32, 6583 (1991).
80. A. Nivlet, V. Le Guen, L. Dechoux, T. Le Gall and C. Mioskowski, Tetrahedron Lett., 39, 2115 (1998);
81. A. Nivlet, L. Dechoux, T. Le Gall and C. Mioskowski, Ear. J. Org. Chem., 3251 (1999).
82. R. Beerli, E.J. Brunner and H.-J. Borschberg, Tetrahedron Lett., 33, 6449 (1992).
83. A. Grob, Angew. Chem. Int. Ed. Engl., 8, 535 (1965).
84. E. Hasegawa, M. Takahashi and T. Horaguchi, Tetrahedron Lett., 36, 5215 (1995).
85. E. Hasegawa, T. Kitazume, K. Suzuki and E. Tosaka, Tetrahedron Lett., 39, 4059 (1998).
86. S. Cristol and R. V. Barbour, J. Am. Chem. Soc., 90, 2832 (1968);
87. A. L. J. Beckwith and G. J. Philliou, J. Chem. Soc. Chem Commun., 658 (1971);
88. A. L. J. Beckwith and G. J. Philliou, Aust. J. Chem., 29, 123 (1976);
89. E. C. Friedrich and R. L. Holmstead, J. Org. Chem., 36, 971 (1971);
90. K. U. Ingold and J. C. Walton, Acc. Chem. Res., 19, 72 (1986).
91. P. H. Lee and J. Lee, Tetrahedron Lett., 39, 7889 (1998).
92. R. J. Boffey, W. G. Whittingham and J. D. Kilbum, J. Chem. Soc., Perkin Trans. 1, 487
93. R. J. Boffey, M. Santagostino, W. G. Whittingham and J. D. Kilbum, J. Chem. Soc., Chem. Commun., 1875, (1998);
94. R. J. Bofey, W. G. Whittingham and J. D. Kilburn, Tetrahedron Lett., 40, 5625 (1999)
95. H. M. Walborsky and M. Topolski, J. Org. Chem., 57, 370 (1992).
96. V. Reutrakul, R. Saeeng, M. Pohmakotr and P. Kongsaeree, Tetrahedron Lett., 40, 1019 (1999).
97. T. Imamoto, T. Hatajima and T. Yoshizawa, Tetrahedron Lett., 35, 7805 (1994).
98. M. Yamashita, K. Okuyama, T. Ohhara, I. Kawasaki and S. Ohto, Chem. Pharm. Bull., 43, 708 (1995);
99. M. Yamashita, K. Okuyama, T. Ohhara, I. Kawasaki, K. Sakai, N. Nakata, T. Kawabe, M. Kusumoto and S. Ohto, Chem. Pharm. Bull, 43, 2075 (1995).
100. M. Yamashita, K. Okuyama, T. Ohhara, I. Kawasaki and S. Ohta, Synlett., 547 (1996).
101. A. Haque and S. Ghosh, J. Chem. Soc., Chem. Commun., 2039 (1997).
102. P. Camps, A. E. Lukach and S. Vázquez, Tetrahedron, 57, 2419 (2001).
103. D. B. G. Williams, K. Blann and C. W. Holzapfel, J. Org. Chem., 65, 2834 (2000).
104. Z. Hou, Y. Zhang and Y. Wakatsuki, Bull. Chem. Soc. Jpn. 70, 149 (1997).
105. G. A. Molander, In “Comp. Org. Synth.”, Trost, B. M.; Fleming, I., Eds., Vol. 1, p 251, Pergamon, Oxford, 1991;
106. G. A. Molander and C. Kenny, J. Org. Chem., 53, 2132 (1988).
107. J.-S. Shiue, C.-C. Lin and J.-M. Fang, Tetrahedron Lett., 34, 335 (1993).
108. J.-S. Shiue, C.-C. Lin and J.-M. Fang, J. Org. Chem. 62, 4643 (1997).
109. D. B. G. Williams, K. Blann and C. W. Holzapfel, Unpublished results.
110. D. B. G. Williams, K. Blann and C. W. Holzapfel, J. Chem. Soc., Perkin Trans. 7, 219 (2001).