Stereoselective pinacol coupling of chiral formylferrocene using divalent samarium triflate: Preparation of a new chiral bisferrocenyl oxazoline ligand and its application to asymmetric diels-alder reactions

Organic Letters

Volumn 7, Issue 26, 2005, Pages 5809-5812

  Fukuzawa, Shin Ichi ^a   Yahara, Yuusuke ^a   Kamiyama, Akira ^a   Hara, Masumi ^a   Kikuchi, Satoshi ^a  

^a CHUO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 30144440701     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0523291     Document Type: Article

References (36)

1. For examples, see: (a) Prasad, K. R. K.; Joshi, N. N. Tetrahedron: Asymmetry 1996, 7, 1957-1960.
2. (b) Ishimaru, K.; Monda, K.; Yamamoto, Y.; Akiba, K. Tetrahedron 1998, 54, 727-734.
3. (c) Shido, M.; Koga, K.; Tomioka, K. J. Org. Chem. 1998, 63, 9351-9357.
4. (d) Donnoli, M. I.; Superchi, S.; Rosini, C. J. Org. Chem. 1998, 63, 9392-9395.
5. (e) Ishihara, K.; Nakashima, D.; Hiraiwa, Y.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 24-25.
6. (f) Suemune, H.; Aso, M. J. Synth. Org. Chem., Jpn. 2005, 8, 807-814.
7. (a) Dietl, F.; Merz, A.; Tomahogh, R. Tetrahedron Lett. 1982, 23, 5225-5228.
8. (b) Kawashima, M.; Hirayama, A. Chem. Lett. 1991, 763-766.
9. For examples, see: (a) Takenaka, N.; Xia, G.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 13198-13199.
10. (b) Li, Y.-G.; Tian, Q.-S.; Zhao, J.; Feng, Y.; Li, M.-J.; You, T.-P. Tetrahedron: Asymmetry 2004, 15, 1707-1710.
11. (c) Chatterjee, A.; Bennur, T. H.; Joshi, N. N. J. Org. Chem. 2003, 68, 5668-5671.
12. (d) Bensari, A.; Renaud, J.-L.; Riant, O. Org. Lett. 2001, 3, 3863-3865.
13. (e) Hashimoto, Y.; Mizuno, U.; Matsuoka, H.; Miyaura, T.; Takakura, M.; Yoshimoto, M.; Oshima, K.; Utimoto, K.; Matsubara, S. J. Am. Chem. Soc. 2001, 123, 1503-1504.
14. 2 has recently been tried for enantioselective pinacol coupling using chiral ligands: Aspinall, H. C.; Greeves, N.; Valla, C. Org. Lett. 2005, 7, 1919-1922.
15. (a) Kim, Y. H. Acc. Chem. Res. 2001, 34, 955-962.
16. (b) Kim, S. M.; Byun, I. S.; Kim, Y. H. Angew. Chem., Int. Ed. 2000, 39, 728-731.
17. (c) Fang, J.-M.; Chen, M.-Y.; Shiue, J.-S.; Lu, L.; Hsu, J.-L. Tetrahedron Lett. 2000, 41, 4633-4636.
18. (a) Taniguchi, N.; Uemura, M. Tetrahedron Lett. 1998, 39, 5385-5388;
19. Tetrahedron 1998, 54, 12775-12788.
20. (b) Taniguchi, N.; Uemura, M. J. Am. Chem. Soc. 2000, 122, 8301-8302.
21. Riant, O.; Samuel, O.; Flessner, T.; Tauden, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733-6745.
22. (a) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Chem. Lett. 1994, 1981-1984.
23. (b) Fukuzawa, S.; Mutoh, K.; Tsuchimoto, T.; Hiyama, T. J. Org. Chem. 1996, 61, 5400-5405.
24. (c) Hanamoto, T.; Sugimoto, Y.; Sugino, A.; Inanaga, J. Synlett 1994, 377-378.
25. (d), Mashima, K.; Oshiki, T.; Tani, K. J. Org. Chem. 1998, 63, 7114-7116.
26. 2, and this complex may control the stereoselectivity.
27. Molander, G. A.; Estevez-Braun, A. M. Bull. Soc. Chim. Fr. 1997, 134, 275-282.
28. For reviews for asymmetric Diels-Alder reactions, see: (a) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
29. (b) Evans, D. A.; Johnson, J. S. Diels-Alder Reaction. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, Chapter 33.1.
30. (c) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667.
31. For a review for lanthanide complexes in asymmetric synthesis, see: Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2225.
32. (a) Kobayashi, S. J. Org. Chem. 1994, 59, 3758-3759.
33. (b) Furuno, H.; Hanamoto, T.; Sugimoto, Y.; Inanaga, J. Org. Lett. 2000, 2, 49-52.
34. (c) Inanaga, J.; Sugimoto, Y.; Hanamoto, T. New J. Chem. 1995, 19, 707-712.
35. (d) Fukuzawa, S.; Fujimoto, K.; Komuro, Y.; Matsuzawa, H. Org. Lett. 2002, 4, 707-709.
36. (e) Fukuzawa, S.; Komuro, Y.; Nakano, N.; Obara, S. Tetrahedron Lett. 2003, 44, 3671-3674.