Generation and reactions of samarium carbanions mediated by samarium iodide

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 57, Issue 2, 1999, Pages 127-135

  Kunishima, Munetaka ^a   Tani, Shohei ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

2,3 Sigmatropic rearrangement; Alkylidene carbenes; Barbier reaction; Carbenoids; Grignard reaction; Organohalides; Organosamariums; Reduction; Samarium iodide; Sulfonium ylides

Indexed keywords

EID: 0000754470     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.57.127     Document Type: Article

References (56)

1. (a) H.B. Kagan, J.L. Namy, Tetrahedron, 42, 6573 (1986);
2. (b) H.B. Kagan, New J. Chem., 14, 453 (1990);
3. (c) J.A. Soderquist, Aldrichimica Acta. 24, 15 (1991);
4. (d) G.A. Molander, "Comprehensive Organic Synthesis", Vol.1, eds. by B.M. Trost, I. Fleming, Pergamon, Oxford, 1991, p.251;
5. (e) G. A. Molander, Chem Rev., 92, 29 (1992);
6. (f) G. A. Molander, idem, Org. React., 46, 211 (1994);
7. (g) G.A. Molander, C.R. Harris, Chem. Rev., 96, 307 (1996);
8. (h) T. Skrydstrup, Angew. Chem., Int. Ed. Engl., 36, 345 (1997);
9. (i) G.A. Molander, C.R. Harris, Tetrahedron, 54, 3321 (1998)
10. (a) D.P. Curran, T.L. Fevig, M.J. Totleben, Synlett, 1990, 773;
11. (b) G.A. Molander, L.S. Harring, J. Org. Chem., 55, 6171 (1990);
12. (c) D. P. Curran, M.J. Totleben, J. Am. Chem. Soc., 114, 6050 (1992);
13. (d) D.P. Curran, T.L. Fevig, C.P. Jasperse, M.J. Totleben, Synlett, 1992, 943
14. G.A. Molander, C.R. Harris, J. Am. Chem. Soc., 117, 3705 (1995)
15. G.A. Molander, C.R. Harris, J. Org. Chem., 63, 4374 (1998)
16. J. Inanaga, M. Ishikawa, M. Yamaguchi, Chem. Lett., 1987, 1485
17. M. Matsukawa, J. Inanaga, M. Yamaguchi, Tetrahedron Lett., 28, 5877 (1987)
18. T.L. Fevig, R.L. Elliott, D.P. Curran, J. Am. Chem. Soc., 110, 5064 (1988)
19. M. Kunishima, K. Hioki, T. Ohara, S. Tani, J. Chem. Soc., Chem. Commun., 1992, 219
20. M. Kunishima, K. Hioki, K. Kono, T. Sakuma, S. Tani, Chem. Pharm. Bull., 42, 2190 (1994)
21. D.P. Curran, X. Gu, W. Zhang, P. Dowd, Tetrahedron, 53, 9023 (1997)
22. M. Kunishima, S. Tanaka, K. Kono, K. Hioki, S. Tani, Tetrahedron Lett., 36, 3707 (1995)
23. (a) G. Köbrich, Angew. Chem., Int. Ed. Engl., 6, 41 (1967);
24. (b) P.J. Stang, Chem. Rev., 78, 383 (1978);
25. (c) W. Kirmse, Angew. Chem., Int. Ed. Engl., 36, 1164 (1997)
26. (a) M. Ochiai, M. Kunishima, S. Tani, Y. Nagao, J. Am. Chem. Soc., 113, 3135 (1991);
27. (b) M. Ochiai, K. Uemura, Y. Masaki, J. Am. Chem. Soc., ibid., 115, 2528 (1993)
28. M. Kunishima, K. Hioki, S. Tani, A. Kato, Tetrahedron Lett., 35, 7253 (1994)
29. M.S. Baird, A.G.W. Baxter, A. Hoorfar, I. Jefferies, J. Chem. Soc., Perkin Trans, 1, 1991, 2575
30. (a) R. Brückner, "Comprehensive Organic Synthesis", Vol.6, eds. by B.M. Trost, I. Fleming, Pergamon, Oxford, 1991, p.873;
31. (b) J.A. Marshall, "Comprehensive Organic Synthesis", Vol.3, eds. by B.M. Trost, I. Fleming, Pergamon, Oxford, 1991, p.975;
32. (c) K. Mikami, T. Nakai, Synthesis, 1991, 594 ;
33. (d) T. Nakai, K. Mikami, Org. React., 46, 105 (1994);
34. M. Kunishima, K. Hioki, K. Kono, A. Kato, S. Tani, J. Org. Chem., 62, 7542 (1997)
35. (a) V. Rautenstrauch, J. Chem. Soc., Chem. Commun., 1970, 4;
36. (b) J.E. Baldwin, J. DeBernardis, J.E. Patrick, Tetrahedron Lett., 1970, 353
37. T. Nakai, K. Mikami, S. Taya, Y. Fujita, J. Am. Chem. Soc., 103, 6492 (1981)
38. K. Mikami, Y. Kimura, N. Kishi, T. Nakai, J. Org. Chem., 48, 279 (1983)
39. A. Studer, D.P. Curran, Synlett, 1996, 255
40. (b) K. Hioki, K. Kono, S. Tani, M. Kunishima, Tetrahedron Lett., 39, 5229 (1998)
41. B.M. Trost, L.S. Melvin, Jr., "Sulfur Ylides", Academic Press, New York, 1975
42. M. Kunishima, D. Nakata, C. Goto, K. Hioki, S. Tani, Synlett,
43. Z. Kosarych, T. Cohen, Tetrahedron Lett., 23, 3019 (1982)
44. (a) R. Nomura, T. Matsuno, T. Endo, J. Am. Chem. Soc., 118, 11666 (1996);
45. (b) E.J. Corey, G.Z. Zheng, Tetrahedron Lett., 38, 2045 (1997)
46. B. Hamann-Gaudinet, J.L. Namy, H.B. Kagan, Tetrahedron Lett., 38, 6585 (1997);
47. S. Fukuzawa, K. Mutoh, T. Tsuchimoto, T. Hiyama, J. Org. Chem., 61, 5400 (1996)