Utilization of heterobimetallic complexes as Lewis acids

Tetrahedron Asymmetry

Volumn 9, Issue 8, 1998, Pages 1445-1450

  Morita, Takahiro ^a   Arai, Takayoshi ^b   Sasai, Hiroaki ^b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BINAPHTHOXIDE; LANTHANUM; LANTHANUM TRILITHIUM TRIS 6,6' DIBROMOBINAPHTHOXIDE; LITHIUM; NITROALDOL; UNCLASSIFIED DRUG;

ACID BASE BALANCE; ARTICLE; CATALYSIS; COMPLEX FORMATION; METAL BINDING; PRIORITY JOURNAL; REACTION ANALYSIS; REGULATORY MECHANISM; SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 0032562613     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00124-4     Document Type: Article

References (38)

1. 1. (a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. Review on asymmetric heterobimetallic catalysis:
2. (b) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 1237-1256.
3. 2. For recent publications using heterobimetallic asymmetric catalysts, see (a) Sasai, H.; Bougauchi, M.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 2717-2720.
4. (b) Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783-4784.
5. (c) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem. Int. Ed. Engl. 1997, 36, 1871-1873.
6. (d) Sasai, H.; Hiroi, M.; Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 6031-6034.
7. (e) Takaoka, E.; Yoshikawa, N.; Yamada, Y. M. A.; Sasai, H.; Shibasaki, M. Heterocycles 1997, 46, 157-163.
8. (f) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442.
9. (g) Gröger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, in press.
10. (h) Yamada, K.; Arai, T.; Sasai, H.; Shibasaki, M., submitted for publication.
11. 3. Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 104-106.
12. 4. Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368-1372.
13. 5. (a) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345.
14. (b) Corey, E. J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289-6292.
15. (c) Haase, C.; Sarko, C. R.; DiMare, M. G. Org. Chem. 1995, 60, 1777-1787.
16. (d) Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788-1799.
17. (e) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 6847-6851.
18. (f) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
19. (g) Corey, E. J.; Imai, N.; Zhang, H. Y. J. Am. Chem. Soc. 1991, 113, 728-729.
20. (h) Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 33, 6807-6810.
21. (i) Corey, E. J.; Sarshar, S. J. Am. Chem. Soc. 1992, 114, 7938-7939.
22. (j) Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123-126.
23. (k) Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-7030.
24. (l) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725-1726.
25. (m) Ghosh, A. K.; Mathivanan, P.; Cappiella, J. Tetrahedron Lett. 1996, 37, 3815-3818.
26. (n) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753-1754.
27. (o) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636.
28. (p) Takacs, J. M.; Lawson, E. C.; Reno, M. J.; Youngman, M. A.; Quincy, D. A. Tetrahedron: Asymmetry 1997, 8, 3073-3078.
29. (q) Takacs, J. M.; Quincy, D. A.; Shay, W.; Jones, B. E.; Ross II, C. R. Tetrahedron: Asymmetry 1997, 8, 3079-3087.
30. (r) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E. J. Org. Chem. 1997, 62, 6454-6455.
31. (s) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. J. Org. Chem. 1997, 62, 7937-7941.
32. 6. Addition of 12-crown-4 to AL3B and/or LLB catalyzed Diels-Alder reaction resulted in the formation of 3 with much lower enantiomeric excess (<5% ee). This result also appears to suggest that the lithium cation(s) play a key role in activation of the dienophile.
33. 7. (a) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki M. J. Org. Chem. 1995, 60, 7388-7389. For 6,6′-disubstituted binaphthol in catalytic asymmetric synthesis, see also
34. (b) Terada, M.; Motoyama, Y.; Mikami, K. Tetrahedron Lett. 1994, 35, 6693-6694.
35. 3tris(6,6′-dibromobinaphthoxide) in THF, the coordination of two of each of the THF molecule to lithium atoms other than active site would be reasonable. The forming C-C bond lengths in the S-cis transition state structure of 1 and methyl acrylate, calculated by Houk et al., were taken into account in the reaction of 1 with 2. The geometry of the whole structure other than the forming C-C bond lengths was optimized by UFF calculation. For the transition state, see (a) Pascual-Teresa, B.; Gonzalez, J.; Asensio, A.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 4347-4356. For UFF calculation, see Ref. 1(a) and
36. (b) Rappé, A. K.; Colwell, K. S.; Casewit, C. J. Inorg. Chem. 1993, 32, 3438-3450 and references therein.
37. 3tris(6,6′-dibromobinaphthoxide) complex was also an effective catalyst for the reaction between 1 and 4 in non-polar solvents. (equation presented)
38. 10. Purchased from Kojundo Chemical Laboratory Co., Ltd, 5-1-28 Chiyoda, Sakado-shi, Saitama 350-0214, Japan. Fax: +81-492-84-1351.