Lanthanide Bis-trifluoromethanesulfonylamides as a New Type of Asymmetric Catalysts for Hetero Diels-Alder Reaction with Danishefsky's Diene in the Presence of Water

Synlett

Volumn 1995, Issue 9, 1995, Pages 975-977

  Mikami, Koichi ^a   Kotera, Osamu ^a   Motoyama, Yukihiro ^a   Sakaguchi, Hiroaki ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b CENTRAL GLASS CO LTD   (Japan)

Author keywords

asymmetric catalyst; hetero Diels Alder reaction; lanthanide

Indexed keywords

EID: 2142762098     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5147     Document Type: Article

References (34)

1. Kagan, H. B. Elements in Organic Synthesis in Fundamental and Technological Aspects of Organo-f-Element Chemistry", Marks, T. J.; Fragala, I. L., Eds.; New York; 1985; pp 49-76.
2. Imamoto, T. "Lanthanides in Organic Synthesis"; Academic Press; 1994
3. Molander, G. A. Chem. Rev. 1992, 92, 29.
4. Kobayashi, S. Synlett 1994, 689.
5. Inanaga, J.; Sugimoto, Y.; Hanamoto, T. New J. Chem. in press.
6. Takai, K.; Heathcock, C. H. Org. Chem. 1985, 50, 3247
7. Vougioukas, A. E.; Kagan, H. B. Tetrahedron Lett. 1987, 28, 5513.
8. Gong, L.; Streitwieser, A. J. Org. Chem. 1990, 55, 6235.
9. Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418.
10. Weghe P. V., Collin J. Tetrahedron Lett. 1993, 34, 3881
11. Makioka, Y.; Nakagawa, I.; Taniguchi, Y.; Takai, K.; Fujiwara, Y. Org. Chem. 1993, 58, 4771
12. Bonadies, F.; Lattanzi, A.; Orelli, L. R.; Pesci, S.; Scettri, A. Tetrahedron Lett. 1993, 54, 7649.
13. Quimpere, M.; Jankowski, K. Chem. Soc, Chem. Commun. 1987, 676
14. Marko, I. E.; Evans, G. R.; Declercq, J. P. Tetrahedron 1994, 50, 4557.
15. Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623, and references cited therein.
16. Mikami, K.; Terada, M.; Nakai, T. J. Org. Chem. 1991, 56, 5456.
17. Mikami, K.; Terada, M.; Nakai, T. Tetrahedron: Asymmetry, 1991, 2, 993.
18. Terada, M.; Gu, J.-H.; Deka, D. C; Mikami, K.; Nakai, T. Chem. Lett. 1992, 29.
19. Gu, J.-H.; Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1992, 33, 1465.
20. Mikami, K.; Terada, M.; Nakai, T. Chem. Soc, Chem. Commun. 1993, 343
21. Terada, M.; Nakai, T.; Mikami, K. Inorg. Chim. Acta 1994, (11) 222, 311.
22. Danishefsky, S. Aldrich. Acta 1986, 19, 59.
23. Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
24. Bednarski, M.; Maring, C; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451.
25. Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1986, 108, 7060.
26. Quite recently, Shibasaki et al. have reported the asymmetric catalysis of the Mukaiyama aldol reaction by a similar type of ytterbium bis-Trifylamide: Uotsu, K.; Sasai, H.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 71.
27. We have reported the asymmetric catalysis of the hetero Diels-Alder reaction with Danishefsky's diene by chiral boron trifylamide complexes: Motoyama, Y.; Mikami, K. J. Chem. Soc, Chem. Commun. 1994, 1563.
28. For the use of titanium bis-sulfonamide complexes, see: Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayashi, S. Tetrahedron 1992, 48, 5691
29. Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1991, 111, 5493.
30. For the acidities of trifylamides as strong Bronsted acids, see: Koppel, I. A.; Taft, R. W.; Anvia, F.; Zhu, S.-Z.; Hu, L.-Q. Sung, K.-S.; DesMarteau, D. D.; Yagupolskii, L M.;Yagupolskii, Y. L.; Ignat'ev, N. V.; Kondratenko, N. V. Volkonskii, A. Y.; Vlasov, V. M.; Notario, R.; Maria, P.-C. J. Am. Chem. Soc. 1994, 116, 3047
31. Jurczak, J.; Bauer, T.; Filipek, S.; Tkack, M.; Zygo, K. Chem. Soc, Chem. Commun. 1983, 538
32. Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Date, T.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372.
33. Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851.
34. Mikami, K.; Motoyama, Y.; Terada, M. Am. Chem. Soc. 1994, 116, 2812