Stereoselective preparation of α-hydroxycarboxamide by manganese complex catalyzed hydration of α,β-unsaturated carboxamide with molecular oxygen and phenylsilane

Chemistry Letters

Volumn 33, Issue 10, 2004, Pages 1304-1305

  Sato, Mitsuo ^a   Gunji, Yasuhiko ^a   Ikeno, Taketo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; MANGANESE DERIVATIVE; OXYGEN; SILANE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 11844282141     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1304     Document Type: Article

References (26)

1. a) R. A. Budnik and J. K. Kochi, J. Org. Chem., 41, 1384 (1976).
2. b) T. Yamada, T. Takai, O. Rhode, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 64, 2109 (1991).
3. T. Jintoku, K. Takaki, Y. Fujiwara, Y. Fuchita, and K. Hiraki, Bull. Chem. Soc. Jpn., 63, 438 (1990).
4. T. Yamada, K. Takahashi, K. Kato, T. Takai, S. Inoki, and T. Mukaiyama, Chem. Lett., 1991, 641.
5. I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, and C. J. Urch, Science, 274, 2044 (1996).
6. a) C. Döbler, G. Mehltretter, and M. Beller, Angew. Chem., Int. Ed., 38, 3026 (1999).
7. b) C. Dolbler, G. M. Mehltretter, U. Sundermeier, and M. Beller, J. Am. Chem. Soc., 122, 10289 (2000).
8. M. Sono, M. P. Roach, E. D. Coulter, and J. H. Dawson, Chem. Rev., 96, 2841 (1996).
9. K. Kato, T. Yamada, T. Takai, S. Inoki, and S. Isayama, Bull. Chem. Soc. Jpn., 63, 179 (1990).
10. S. Isayama, Bull. Chem. Soc. Jpn., 63, 1305 (1990).
11. a) S. Isayama and T. Mukaiyama, Chem. Lett., 1989, 1071.
12. b) S. Inoki, K. Kato, S. Isayama, and T. Mukaiyama, Chem. Lett., 1990, 1869.
13. T. Yamada, K. Imagawa, T. Nagata, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 67, 2248 (1994).
14. a) P. Camps, F. Pèrez, and N. Soldevilla, Tetrahedron: Asymmetry, 8, 1877 (1997).
15. b) Y.-Y. Chu, C.-S. Yu, C.-J. Chen, K.-S. Yang, J.-C. Lain, C.-H. Lin, and K. Chen, J. Org. Chem., 64, 6993 (1999).
16. c) E. F. DiMauro and M. C. Koxlowski, Org. Lett., 4, 3781 (2002).
17. d) H. Yu, C. E. Ballard, P. D. Boyle, and B. Wang, Tetrahedron, 58, 7663 (2002) and references therein.
18. a) F. A. Davis and A. C. Sheppard, Tetrahedron, 45, 5703 (1989).
19. b) F. A. Davis and B.-C. Chen, Chem. Rev., 92, 919 (1992).
20. N. Kihara, C. Ollivier, and P. Renaud, Org. Lett., 1, 1419 (1999).
21. 1HNMR analysis.
22. 3 was used throughout the experiment.
23. W. Oppolzer, C. Chapuis, and G. Bernardinelli, Helv. Chim. Acta, 67, 1397 (1984).
24. M. Sato, Y. Gunji, T. Ikeno, and T. Yamada, Synthesis, 2004, 1434.
25. T. Takuyasu, S. Kunikawa, A. Masuyama, and M. Nojima, Org. Lett., 4, 3595 (2002).
26. W. Strub, E. Roduner, and H. Fisher, J. Phys. Chem., 91, 4379 (1987).