Reductive coupling of carbonyl compounds to pinacols by using Sm-I2MeOH or Sm-I2-Ti(O(i)Pr)4-MeOH systems

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3271-3274

  Yanada, Reiko ^a   Negoro, Nobuyuki ^a   Yanada, Kazuo ^b   Fujita, Tetsuro ^b  

^a KYOTO UNIVERSITY   (Japan)

^b SETSUNAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKANEDIOL DERIVATIVE;

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

EID: 0030944453     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00600-X     Document Type: Article

References (32)

1. Kagan, H. B.; Namy, J. L. Tetrahedron, 1986,42, 6573-6614. Kagan, H. B. Nouv. J. Chim., 1990, 14, 453-460. Molander, G. A. Chem. Rev., 1992, 92, 29-68. Molander, G. A. Organic Reactions, 1994, 46, 211-367. Molander, G. A.; Harris, C. R. Chem. Rev., 1996, 96, 307-338.
2. Kagan, H. B.; Namy, J. L. Tetrahedron, 1986,42, 6573-6614. Kagan, H. B. Nouv. J. Chim., 1990, 14, 453-460. Molander, G. A. Chem. Rev., 1992, 92, 29-68. Molander, G. A. Organic Reactions, 1994, 46, 211-367. Molander, G. A.; Harris, C. R. Chem. Rev., 1996, 96, 307-338.
3. Kagan, H. B.; Namy, J. L. Tetrahedron, 1986,42, 6573-6614. Kagan, H. B. Nouv. J. Chim., 1990, 14, 453-460. Molander, G. A. Chem. Rev., 1992, 92, 29-68. Molander, G. A. Organic Reactions, 1994, 46, 211-367. Molander, G. A.; Harris, C. R. Chem. Rev., 1996, 96, 307-338.
4. Kagan, H. B.; Namy, J. L. Tetrahedron, 1986,42, 6573-6614. Kagan, H. B. Nouv. J. Chim., 1990, 14, 453-460. Molander, G. A. Chem. Rev., 1992, 92, 29-68. Molander, G. A. Organic Reactions, 1994, 46, 211-367. Molander, G. A.; Harris, C. R. Chem. Rev., 1996, 96, 307-338.
5. Kagan, H. B.; Namy, J. L. Tetrahedron, 1986,42, 6573-6614. Kagan, H. B. Nouv. J. Chim., 1990, 14, 453-460. Molander, G. A. Chem. Rev., 1992, 92, 29-68. Molander, G. A. Organic Reactions, 1994, 46, 211-367. Molander, G. A.; Harris, C. R. Chem. Rev., 1996, 96, 307-338.
6. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, L; Sonoda, N. Chem. Lett., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487 and references cited therein.
7. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, L; Sonoda, N. Chem. Lett., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487 and references cited therein.
8. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, L; Sonoda, N. Chem. Lett., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487 and references cited therein.
9. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, L; Sonoda, N. Chem. Lett., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487 and references cited therein.
10. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, L; Sonoda, N. Chem. Lett., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487 and references cited therein.
11. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, L; Sonoda, N. Chem. Lett., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487 and references cited therein.
12. Yanada, R.; Bessho, K.; Yanada, K. Synlett, 1995, 443-444.
13. Yanada, R.; Negoro, N.; Bessho, K.; Yanada, K. Synlett, 1995, 1261-1263.
14. Yanada, R.; Negoro, N.; Yanada, K.; Fujita, T. Tetrahedron Lett., 1996, 37, 9313-9316.
15. Namy, J. L.; Kagan, H. B. Tetrahedron Lett., 1983, 24, 765-766.
16. Girard, P.; Namy, J. L.; Kagan, H. B. J Am. Chem. Soc., 1980, 102, 2693-2698.
17. 1H-NMR (270 MHz) analysis. The proton a to the hydroxy group in dl-isomer appears at ca. 0.1-0.2 ppm higher field than the one in meso-isomer. Handa, Y.; Inanaga, J. Tetrahedron Lett., 1987, 28, 5717-5718.
18. 2 in THF. Ref. 6.
19. 3CN. Akane, N; Kanagawa, Y; Nishiyama, Y; Ishii, Y. Chem. Lett., 1992, 2431-2434, Akane, N.; Hatano, T; Kusui, H; Nishiyama, Y; Ishii, Y. J. Org. Chem., 1994, 59, 7902-7907.
20. 3CN. Akane, N; Kanagawa, Y; Nishiyama, Y; Ishii, Y. Chem. Lett., 1992, 2431-2434, Akane, N.; Hatano, T; Kusui, H; Nishiyama, Y; Ishii, Y. J. Org. Chem., 1994, 59, 7902-7907.
21. 3 catalyzed electrochemical coupling: Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun., 1989, 276-277.
22. 3 catalyzed electrochemical coupling: Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun., 1989, 276-277.
23. 3 catalyzed electrochemical coupling: Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun., 1989, 276-277.
24. 3 catalyzed electrochemical coupling: Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun., 1989, 276-277.
25. 3 catalyzed electrochemical coupling: Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun., 1989, 276-277.
26. 3 catalyzed electrochemical coupling: Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun., 1989, 276-277.
27. Probably this results may be attributed to the difference in stability between the radical intermediates. Because a benzyl radical intermediate from an aromatic carbonyl compound is stabilized by the neighboring aromatic ring, it has enough time to react with another radical intermediate to give diol. The less stable radical intermediate from the aliphatic one may abstract the hydrogen radical from the solvent methanol more rapidly than react with another radical intermediate.
28. 2-Barden, M. C.; Schwartz, J. J. Am. Chem. Soc., 1996, 118, 5484-5485, Clerici, A; Clerici, L.; Porta, O. Tetrahedron Lett., 1996, 37, 3035-3038.
29. 2-Barden, M. C.; Schwartz, J. J. Am. Chem. Soc., 1996, 118, 5484-5485, Clerici, A; Clerici, L.; Porta, O. Tetrahedron Lett., 1996, 37, 3035-3038.
30. Gary, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd Ed., Part A, Plenum Press, New York and London, 1990, 201.
31. Alcohol was formed mainly in the presence of an excess of Sm. Olivier, H.; Chauvin, Y.; Saussine, L. Tetrahedron, 1989, 45,165-169.
32. Clerici, A. ; Porta, O. J. Org. Chem., 1985, 50, 76-81.