Samarium(II) iodide-induced tandem reductive coupling-Dieckmann condensation reaction: One-step synthesis of bicyclic oxacyclopentanecarboxylate from bis-α,β-unsaturated esters

Tetrahedron Letters

Volumn 44, Issue 25, 2003, Pages 4649-4652

  Shinohara, Ikuo ^a   Okue, Masayuki ^b,c   Yamada, Yasuji ^b   Nagaoka, Hiroto ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^c MEIJI SEIKA KAISHA LTD   (Japan)

Author keywords

Annulation; Cyclopentanones; Radicals and radical reactions; Samarium and compounds

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; OXACYCLOPENTANE CARBOXYLATE; SAMARIUM; SAMARIUM DIIODIDE; SAMARIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CYCLIZATION; DIECKMANN REACTION; DIMERIZATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038101598     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01093-1     Document Type: Article

References (29)

1. Klemm L.H., Olson D.R. J. Org. Chem. 38:1973;3390-3394.
2. Nishiguchi I., Hirashima T. Angew. Chem., Int. Ed. Engl. 22:1983;52-53.
3. Kise N., Mashiba S., Uda N. J. Org. Chem. 63:1998;7931-7938.
4. Kise N., Iitaka S., Iwasaki K., Uda N. J. Org. Chem. 67:2002;8305-8315.
5. Takaki K., Beppu F., Tanaka S., Tsubaki Y., Jintoku T., Fujiwara Y. J. Chem. Soc., Chem. Commun. 1990;516-517.
6. Totton E.L., Camp N.C. III, Cooper G.M., Haywood B.D., Lewis D.P. J. Org. Chem. 32:1967;2033-2034.
7. 2: (a) Molander, G. A.; Huérou, Y. L.; Brown, G. A. J. Org. Chem. 2001, 66, 4511-4516; (b) Sono, M.; Nakashiba, Y.; Nakashima, K.; Tori, M. J. Org. Chem. 2000, 65, 3099-3106; (c) Molander, G. A.; Wolfe, C. N. J. Org. Chem. 1998, 63, 9031-9036.
8. 2: (a) Molander, G. A.; Huérou, Y. L.; Brown, G. A. J. Org. Chem. 2001, 66, 4511-4516; (b) Sono, M.; Nakashiba, Y.; Nakashima, K.; Tori, M. J. Org. Chem. 2000, 65, 3099-3106; (c) Molander, G. A.; Wolfe, C. N. J. Org. Chem. 1998, 63, 9031-9036.
9. 2: (a) Molander, G. A.; Huérou, Y. L.; Brown, G. A. J. Org. Chem. 2001, 66, 4511-4516; (b) Sono, M.; Nakashiba, Y.; Nakashima, K.; Tori, M. J. Org. Chem. 2000, 65, 3099-3106; (c) Molander, G. A.; Wolfe, C. N. J. Org. Chem. 1998, 63, 9031-9036.
10. Inanaga J., Handa Y., Tabuchi T., Otsubo K. Tetrahedron Lett. 32:1991;6557-6558.
11. Hon Y.-S., Chu K.-P., Hong P.-C., Lu L. Synth. Commun. 22:1992;429-443.
12. Ogawa A., Takami N., Sekiguchi M., Ryu I., Kambe N., Sonoda N. J. Am. Chem. Soc. 114:1992;8729-8730.
13. Ogawa A., Nanke T., Takami N., Sumino Y., Ryu I., Sonoda N. Chem. Lett. 1994;379-380.
14. Murakami M., Hayashi M., Ito Y. Synlett. 1994;179-180.
15. Ogawa A., Nanke T., Takami N., Sekiguchi M., Kambe N., Sonoda N. Appl. Organomet. Chem. 9:1995;461-466.
16. Ogawa A., Takami N., Nanke T., Ohya S., Hirano T., Sonoda N. Tetrahedron. 53:1997;12895-12902.
17. Taber D.F., Wang Y. J. Am. Chem. Soc. 119:1997;22-26.
18. 2-Sm treatment.
19. 17 NaH, THF, -78°C to rt.
20. 1H NMR.
21. Moüns L., Baizer M.M., Little R.D. J. Org. Chem. 51:1986;4497-4498.
22. Cane D.E., Thomas P.J. J. Am. Chem. Soc. 106:1984;5295-5303.
23. 1H NMR.
24. Brown H.C., Periasamy M. J. Org. Chem. 46:1981;3166-3170.
25. Brown H.C., Rothberg I., Vander Jagt D.L. J. Org. Chem. 37:1972;4098-4100.
26. 2O at 140°C.
27. Ando K. J. Org. Chem. 64:1999;8406-8408.
28. Shiao M.-J., Liang D., Ku C.-S., Yang C.-H. Synth. Commun. 18:1988;1553-1563.
29. Warshawsky A., Fuchs B. Tetrahedron. 25:1969;2633-2646.