Design of bronsted acid-assisted chiral Lewis acid (BLA) catalysts for highly enantioselective Diels-Alder reactions

Journal of the American Chemical Society

Volumn 120, Issue 28, 1998, Pages 6920-6930

  Ishihara, Kazuaki ^a   Kurihara, Hideki ^a   Matsumoto, Masayuki ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CATALYSIS; CHIRALITY; HYDROGEN BOND; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032558078     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9810282     Document Type: Article

References (59)

1. For recent reviews, see: (a) Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: London, 1995; Vol. 1, p 29. (b) Ishihara, K.; Yamamoto, H. CatTech 1997, 51. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289.
2. For recent reviews, see: (a) Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: London, 1995; Vol. 1, p 29. (b) Ishihara, K.; Yamamoto, H. CatTech 1997, 51. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289.
3. For recent reviews, see: (a) Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: London, 1995; Vol. 1, p 29. (b) Ishihara, K.; Yamamoto, H. CatTech 1997, 51. (c) Dias, L. C. J. Braz. Chem. Soc. 1997, 8, 289.
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5. 2: (g) Reetz, M. T.; Kyung, S. H.; Bolm, C.; Zierke, T. Chem. Ind. (London) 1986, 2409. (h) Mikami, K.; Motoyama, Y.; Nakai. T. Tetrahedron: Asymmetry 1991, 2, 643. (i) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (j) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967. (k) Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron: Asymmetry 1996, 7, 2479. (l) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
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7. 2: (g) Reetz, M. T.; Kyung, S. H.; Bolm, C.; Zierke, T. Chem. Ind. (London) 1986, 2409. (h) Mikami, K.; Motoyama, Y.; Nakai. T. Tetrahedron: Asymmetry 1991, 2, 643. (i) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (j) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967. (k) Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron: Asymmetry 1996, 7, 2479. (l) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
8. 2: (g) Reetz, M. T.; Kyung, S. H.; Bolm, C.; Zierke, T. Chem. Ind. (London) 1986, 2409. (h) Mikami, K.; Motoyama, Y.; Nakai. T. Tetrahedron: Asymmetry 1991, 2, 643. (i) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (j) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967. (k) Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron: Asymmetry 1996, 7, 2479. (l) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
9. 2: (g) Reetz, M. T.; Kyung, S. H.; Bolm, C.; Zierke, T. Chem. Ind. (London) 1986, 2409. (h) Mikami, K.; Motoyama, Y.; Nakai. T. Tetrahedron: Asymmetry 1991, 2, 643. (i) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (j) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967. (k) Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron: Asymmetry 1996, 7, 2479. (l) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
10. 2: (g) Reetz, M. T.; Kyung, S. H.; Bolm, C.; Zierke, T. Chem. Ind. (London) 1986, 2409. (h) Mikami, K.; Motoyama, Y.; Nakai. T. Tetrahedron: Asymmetry 1991, 2, 643. (i) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (j) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967. (k) Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron: Asymmetry 1996, 7, 2479. (l) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
11. 2: (g) Reetz, M. T.; Kyung, S. H.; Bolm, C.; Zierke, T. Chem. Ind. (London) 1986, 2409. (h) Mikami, K.; Motoyama, Y.; Nakai. T. Tetrahedron: Asymmetry 1991, 2, 643. (i) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (j) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967. (k) Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron: Asymmetry 1996, 7, 2479. (l) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
12. 2: (g) Reetz, M. T.; Kyung, S. H.; Bolm, C.; Zierke, T. Chem. Ind. (London) 1986, 2409. (h) Mikami, K.; Motoyama, Y.; Nakai. T. Tetrahedron: Asymmetry 1991, 2, 643. (i) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (j) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967. (k) Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron: Asymmetry 1996, 7, 2479. (l) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
13. 2: (g) Reetz, M. T.; Kyung, S. H.; Bolm, C.; Zierke, T. Chem. Ind. (London) 1986, 2409. (h) Mikami, K.; Motoyama, Y.; Nakai. T. Tetrahedron: Asymmetry 1991, 2, 643. (i) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (j) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967. (k) Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron: Asymmetry 1996, 7, 2479. (l) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
14. 2: (g) Reetz, M. T.; Kyung, S. H.; Bolm, C.; Zierke, T. Chem. Ind. (London) 1986, 2409. (h) Mikami, K.; Motoyama, Y.; Nakai. T. Tetrahedron: Asymmetry 1991, 2, 643. (i) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (j) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967. (k) Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron: Asymmetry 1996, 7, 2479. (l) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
15. 2: (g) Reetz, M. T.; Kyung, S. H.; Bolm, C.; Zierke, T. Chem. Ind. (London) 1986, 2409. (h) Mikami, K.; Motoyama, Y.; Nakai. T. Tetrahedron: Asymmetry 1991, 2, 643. (i) Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (j) Motoyama, Y.; Terada, M.; Mikami, K. Synlett 1995, 967. (k) Harada, T.; Takeuchi, M.; Hatsuda, M.; Ueda, S.; Oku, A. Tetrahedron: Asymmetry 1996, 7, 2479. (l) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1997, 8, 815.
16. (a) Hawkins, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794. Hawkins, J. M.; Loren, S.; Nambu, M. J. Am. Chem. Soc. 1994, 116, 1657. (b) Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966. Corey, E. J.; Loh, T.-P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290. (c) Ishihara, K.; Gao, Q.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10412.
17. (a) Hawkins, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794. Hawkins, J. M.; Loren, S.; Nambu, M. J. Am. Chem. Soc. 1994, 116, 1657. (b) Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966. Corey, E. J.; Loh, T.-P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290. (c) Ishihara, K.; Gao, Q.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10412.
18. (a) Hawkins, J. M.; Loren, S. J. Am. Chem. Soc. 1991, 113, 7794. Hawkins, J. M.; Loren, S.; Nambu, M. J. Am. Chem. Soc. 1994, 116, 1657. (b) Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966. Corey, E. J.; Loh, T.-P.; Roper, T. D.; Azimioara, M. D.; Noe, M. C. J. Am. Chem. Soc. 1992, 114, 8290. (c) Ishihara, K.; Gao, Q.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 10412.
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