(Arene)tricalbonylchromium complexes in radical reactions: Samarium(XI) iodide-mediated coupling of chromium-complexed benzaldehyde or acetophenone with methyl acrylate

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7199-7202

  Taniguchi, Nobukazu ^a   Uemura, Motokazu ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG PURITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

ARENE;

EID: 0030667914     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01714-0     Document Type: Article

References (36)

1. For some reviews; (a) Smadja, W. Synlett 1994, 1-26.
2. (b) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296-304.
3. (c) Molander, G. A.; Harris, C. H. Chem. Rev. 1996, 96, 307-338.
4. For some representative references; (a) Kito, M.; Sakai, T.; Yamada, K.; Matsuda, F.; Shirahama, H. Synlett, 1993, 158-160.
5. (b) Kawatsura, M.; Matsuda, F.; Shirahama, H. J. Org. Chem. 1994, 59, 6900-6901.
6. (c) Kawatsura, M. Dekura, F.; Shirahama, H.; Matsuda, F. Synlett 1996, 373-376.
7. (d) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447-6449.
8. (e) M. Kito, T. Sakai, N. Haruta, H. Shirahama, F. Matsuda, Synlett 1996, 1057-1060.
9. (f) M. Kito, T. Sakai, M. Miyashita, F. Matsuda, Synlett 1997, 219-220.
10. (g) Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265-1276 and references therein.
11. For some representative references; (a) Toru, F.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464-10465.
12. (b) Yamamoto, Y.; Onuku, S.; Yumoto, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 421-422.
13. (c) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamamura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455-6456.
14. (d) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576-3577.
15. (f) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc. Chem. Commun. 1995, 481-482.
16. (g) M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779-10780.
17. (f) Wu, J. H.; Radinov, R.; Poter, N. A. J. Am. Chem. Soc. 1995, 117, 11029-11030.
18. (g) Guindon, Y.; Guérin, B.; Chabot, C.; Mackintosh, N.; Ogilivie, W. W. Synlett 1995, 449-451.
19. (j) Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200-9201.
20. (h) Gerster, M.; Schenk, K.; Renaud, P. Angew. Chem. Int. Ed. Engl. 1996, 35, 2396-2398.
21. (i) Nishida, M.; Nishida, A.; Kawahara, N. J. Org. Chem. 1996, 61, 3574-3575.
22. (j) Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200-9201 and references therein.
23. For γ-lactones; (a) Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc. Chem. Commun. 1986, 624-625; J. Chem. Soc. Perkin Trans. 1 1988, 1669-1675.
24. For γ-lactones; (a) Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. J. Chem. Soc. Chem. Commun. 1986, 624-625; J. Chem. Soc. Perkin Trans. 1 1988, 1669-1675.
25. (b) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 5763-5764.
26. (c) Inanaga, J.; Ujikawa, O.; Handa, Y.; Otsubo, K.; Yamaguchi, S. J. Alloys Compd 1993, 192, 197-199. see also ref. 1(c), 2(b) and 2(c).
27. Dihydronaphthalene chromium with a ketone function gave a cyclization product via a ketyl radical; Schmalz, H-G.; Siegel, S.; Bats, J. W. Angew. Chem. Int. Ed. Engl. 1995, 34, 2383-2385.
28. Fukuzawa, S.; Seki, K.; Tatsuzawa, M.; Muthoh, K. J. Am. Chem. Soc. 1997, 119, 1482-1483.
29. (a) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088-6089.
30. (b) Taniguchi, N.; Uemura, M. Synlett 1997, 51-53.
31. Solladié-Cavallo, A. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, 1989, Vol. 1, pp 99-133.
32. Besançon, J.; Card, A.; Dusausoy, Y.; Tirouflet, J. C. R. Acad. Sci. Paris, Ser. C, 1972, 274, 545-548. Besançon, J.; Tirouflet, J.; Card, A.; Dusausoy, Y. J. Orgnomet. Chem. 1973, 59, 267-279.
33. Besançon, J.; Card, A.; Dusausoy, Y.; Tirouflet, J. C. R. Acad. Sci. Paris, Ser. C, 1972, 274, 545-548. Besançon, J.; Tirouflet, J.; Card, A.; Dusausoy, Y. J. Orgnomet. Chem. 1973, 59, 267-279.
34. 3 of the reaction conditions in the presence or absence of the Lewis acid, and was explained to be caused by the distinct conformations; Davies, S. G.; Goodfellow, C. L. Synlett, 1989, 59-62; J. Chem. Soc. Perkin Trans. 1 1990, 393-407.
35. 3 of the reaction conditions in the presence or absence of the Lewis acid, and was explained to be caused by the distinct conformations; Davies, S. G.; Goodfellow, C. L. Synlett, 1989, 59-62; J. Chem. Soc. Perkin Trans. 1 1990, 393-407.
36. 2. The sign of optical rotations is correlated to the carbonyl oxygen anti-or syn-conformation of tricarbonylchromium-complexed benzaldehydes or aryl alkylketones; see ref. 9.