Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α,β-Unsaturated Aldehydes Catalyzed by Cationic 3-Oxobutylideneaminatocobalt(III) Complexes

Bulletin of the Chemical Society of Japan

Volumn 76, Issue 11, 2003, Pages 2197-2207

  Kezuka, Satoko ^a,b   Ohtsuki, Natsuki ^a   Mita, Tsuyoshi ^a   Kogami, Youichi ^a   Ashizawa, Tomoko ^a   Ikeno, Taketo ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

^b AOYAMA GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSTS; NITROGEN COMPOUNDS; POSITIVE IONS; UNSATURATED COMPOUNDS; X RAY DIFFRACTION ANALYSIS;

DIPOLAR CYCLOADDTION REACTION; ENANTIOSELECTIVITY;

ALDEHYDES;

3 OXOBUTYLIDENEAMINATOCOBALT; ALDEHYDE DERIVATIVE; ANTIMONY; CATION; COBALT COMPLEX; ISOXAZOLIDINE DERIVATIVE; NITRONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY; REACTION ANALYSIS; TEMPERATURE DEPENDENCE; X RAY ANALYSIS;

EID: 0345528016     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.76.2197     Document Type: Article

References (42)

1. a) J. J. Tufariello, "1,3-Dipolar Cycloaddition Chemistry," ed by A. Padwa, Wiley, New York (1984), Vol. 2, p. 83.
2. K. B. G. Trossell, "Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis," VCH, New York (1988).
3. "Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products," ed by A. Padwa and P. W. Pearson, Wiley & Sons, New York (2002).
4. R. Huisgen, Angew. Chem., 75, 604 (1963).
5. M. Fredrickson, Tetrahedron, 53, 403 (1997).
6. S. Kanemasa, T. Uemura, and E. Wada, Tetrahedron Lett., 33, 7889 (1992).
7. a) K. V. Gothelf and K. A. Joørgensen, J. Org. Chem., 59, 5687 (1994).
8. K. V. Gothelf, R. G. Hazell, and K. A. Joørgensen, J. Org. Chem., 61, 346 (1996).
9. S. Crosignani, G. G. Desimoni, G. Faita, S. Fillippone, A. Mortoni, P. Righetti, and M. Zema, Tetrahedron Lett., 40, 7007 (1999).
10. A. I. Sanchez-Blanco, K. V. Gothelf, and K. A. Joørgensen, Tetrahedron Lett., 38, 7923 (1997).
11. S. Kobayashi and M. Kawamura, J. Am. Chem. Soc., 120, 5840 (1998).
12. S. Kanemasa, Y. Oderaotoshi, J. Tanaka, and E. Wada, J. Am. Chem. Soc., 120, 12355 (1998).
13. K. Hori, H. Kodama, T. Ohta, and I. Furukawa, J. Org. Chem., 64, 5017 (1999).
14. S. Iwasa, S. Tsushima, T. Shimada, and H. Nishiyama, Tetrahedron, 58, 227 (2002).
15. a) J.-P. G. Seerden, A. W. A. Scholte op Reimer, and H. W. Scheeren, Tetrahedron Lett., 35, 4419 (1994).
16. J.-P. G. Seerden, M. M. M. Boeren, and H. W. Scheeren, Tetrahedron, 53, 11843 (1997).
17. K. B. Jensen, R. G. Hazell, and K. A. Joørgensen, J. Org. Chem., 64, 2353 (1999).
18. K. B. Simonsen, P. Bayón, R. G. Hazell, K. V. Gothelf, and K. A. Joørgensen, J. Am. Chem. Soc., 121, 3845 (1999).
19. K. B. Jensen, K. V. Gothelf, R. G. Hazell, and K. A. Joørgensen, J. Org. Chem., 62, 2471 (1997).
20. a) M. Shirahase, Y. Oderaotoshi, and S. Kanemasa, The 78th Annual Meeting of the Chemical Society of Japan, March 2000, 4G1 08, Funabashi, Japan.
21. M. Shirahase and S. Kanemasa, The 80th Annual Meeting of the Chemical Society of Japan, March 2001, 2H6 08 and 2H6 09, Kobe, Japan.
22. S. Kanemasa, "Cycloaddition Reaction in Organic Synthesis," ed by S. Kobayashi and K. A. Joørgensen, Wiley-VCH, Weinheim (2002), p. 274.
23. F. Viton, G. Bernardinelli, and E. P. Kündig, J. Am. Chem. Soc., 124, 4968 (2002).
24. W. S. Jen, J. J. M. Wiener, and D. W. C. MacMillan, J. Am. Chem. Soc., 122, 9874 (2000).
25. a) T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 34, 2145 (1995).
26. K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem. Lett., 1997, 493.
27. T. Yamada, Y. Ohtsuka, and T. Ikeno, Chem. Lett., 1998, 1129.
28. a) T. Yamada, T. Ikeno, H. Sekino, and M. Sato, Chem. Lett., 1999, 719. b) T. Ikeno, M. Sato, and T. Yamada, Chem. Lett., 1999, 1345.
29. a) T. Yamada, T. Ikeno, H. Sekino, and M. Sato, Chem. Lett., 1999, 719. b) T. Ikeno, M. Sato, and T. Yamada, Chem. Lett., 1999, 1345.
30. T. Ikeno, A. Nishizuka, M. Sato, and T. Yamada, Synlett, 2001, 406.
31. T. Ikeno, M. Sato, H. Sekino, A. Nishizuka, and T. Yamada, Bull. Chem. Soc. Jpn., 74, 2139 (2001).
32. T. Yamada, S. Kezuka, T. Mita, and T. Ikeno, Heterocycles, 52, 1041 (2000).
33. a) S. Kezuka, T. Mita, N. Ohtsuki, T. Ikeno, and T. Yamada, Chem. Lett., 2000, 824.
34. S. Kezuka, T. Mita, N. Ohtsuki, T. Ikeno, and T. Yamada, Bull. Chem. Soc. Jpn., 74, 1333 (2001).
35. a) S. Kezuka, T. Ikeno, and T. Yamada, Org. Lett., 3, 1937 (2001).
36. S. Kezuka, Y. Kogami, T. Ikeno, and T. Yamada, Bull. Chem. Soc. Jpn., 76, 49 (2003).
37. 4 treatment in the reaction of 1a and 2a catalyzed by the complex 4e (Entry 5, Table 1), the resulting aldehyde was isolated by the rapid work-up in 81% yield with 99% endo-selectivity and 51% ee. In this article, the chemical yield, diastereoselectivity, and enantioselectivity listed in Tables 1-5 were determined as the corresponding alcohol obtained after reductive quenching.
38. S. Kanemasa, Nippon Kágaku Kaishi, 2000, 155.
39. a) O. Kamm, Org. Synth. Coll. Vol. 2, 445 (1941).
40. O. H. Wheeler and P. H. Gore, J. Am. Chem. Soc., 78, 3363 (1956).
41. J. B. Brown, H. B. Henbest, and E. R. H. Jones, J. Chem. Soc., 1950, 3634.
42. J. L. Roberts, P. S. Borromeo, and C. D. Poulter, Tetrahedron Lett., 19, 1621 (1977).