The first enantioselective aza-Diels-Alder reactions of imino dienophiles on use of a chiral zirconium catalyst

Angewandte Chemie - International Edition

Volumn 37, Issue 7, 1998, Pages 979-981

  Kobayashi, Shu ^a   Komiyama, Susumu ^a   Ishitani, Haruro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Asymmetric catalysis; Cycloadditions; Homogeneous catalysis; Lewis acids; Zirconium

Indexed keywords

EID: 0031980938     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980420)37:7<979::AID-ANIE979>3.0.CO;2-5     Document Type: Article

References (36)

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8. For example, a) E. Borrione, M. Prato, G. Scorrano, M. Stiranello, J. Chem. Soc. Perkin Trans. 1 1989, 2245-2250; b) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1455-1457; Angew. Chem. Int. Ed. Engl. 1990, 29, 1468-1471; c) P. D. Bailey, D. J. Londesbrough, T. C. Hancox, J. D. Heffernan, A. B. Holmes, J. Chem. Soc. Chem. Commun. 1994, 2543-2544; d) A. K. McFarlane, G. Thomas, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 2803-2808; e) E. P. Kündig, L. H. Xu, P. Romanens, G. Bernardinelli, Synlett 1996, 270-272.
9. For example, a) E. Borrione, M. Prato, G. Scorrano, M. Stiranello, J. Chem. Soc. Perkin Trans. 1 1989, 2245-2250; b) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1455-1457; Angew. Chem. Int. Ed. Engl. 1990, 29, 1468-1471; c) P. D. Bailey, D. J. Londesbrough, T. C. Hancox, J. D. Heffernan, A. B. Holmes, J. Chem. Soc. Chem. Commun. 1994, 2543-2544; d) A. K. McFarlane, G. Thomas, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 2803-2808; e) E. P. Kündig, L. H. Xu, P. Romanens, G. Bernardinelli, Synlett 1996, 270-272.
10. For example, a) E. Borrione, M. Prato, G. Scorrano, M. Stiranello, J. Chem. Soc. Perkin Trans. 1 1989, 2245-2250; b) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1455-1457; Angew. Chem. Int. Ed. Engl. 1990, 29, 1468-1471; c) P. D. Bailey, D. J. Londesbrough, T. C. Hancox, J. D. Heffernan, A. B. Holmes, J. Chem. Soc. Chem. Commun. 1994, 2543-2544; d) A. K. McFarlane, G. Thomas, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 2803-2808; e) E. P. Kündig, L. H. Xu, P. Romanens, G. Bernardinelli, Synlett 1996, 270-272.
11. For example, a) E. Borrione, M. Prato, G. Scorrano, M. Stiranello, J. Chem. Soc. Perkin Trans. 1 1989, 2245-2250; b) H. Waldmann, M. Braun, M. Dräger, Angew. Chem. 1990, 102, 1455-1457; Angew. Chem. Int. Ed. Engl. 1990, 29, 1468-1471; c) P. D. Bailey, D. J. Londesbrough, T. C. Hancox, J. D. Heffernan, A. B. Holmes, J. Chem. Soc. Chem. Commun. 1994, 2543-2544; d) A. K. McFarlane, G. Thomas, A. Whiting, J. Chem. Soc. Perkin Trans. 1 1995, 2803-2808; e) E. P. Kündig, L. H. Xu, P. Romanens, G. Bernardinelli, Synlett 1996, 270-272.
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17. For the use of 6,6′-dihromo-1,1′-bi-2-naphthol, see a) M. Terada, Y. Motoyama, K. Mikami, Tetrahedron Lett. 1994, 35, 6693-6696; b) H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh, M. Shibasaki, J. Org. Chem. 1995, 60, 7388-7389.
18. For the use of 6,6′-dihromo-1,1′-bi-2-naphthol, see a) M. Terada, Y. Motoyama, K. Mikami, Tetrahedron Lett. 1994, 35, 6693-6696; b) H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh, M. Shibasaki, J. Org. Chem. 1995, 60, 7388-7389.
19. a) S. Danishefsky, T. Khahara, J. Am. Chem. Soc. 1974, 96, 7807-7809;
20. b) J. F. Kerwin, Jr., S. Danishefsky, Tetrahedron Lett. 1982, 23, 3739-3742.
21. [4. 5] When the aldimine prepared from aniline or 2-methoxyaniline was used under the same reaction conditions, the corresponding pyridone derivatives were obtained in good yields but low enantiomeric excesses (aniline: 68% yield, 4% ee; 2-methoxyaniline: 74% yield, 25% ee).
22. S. Danishefsky, M. Bednarski, T. Izawa, C. Maring, J. Org. Chem. 1984, 49, 2290-2292.
23. The solvents influence the structure of the catalyst: details of the structure are now under investigation. See also L. F. Tietz, P. Saling, Chirality 1993, 5, 329-333.
24. S. Kobayashi, S. Komiyama, H. Ishitani, unpublished results.
25. Titanium(IV)-1,1′-bi-2-naphthol complexes were used in some asymmetric reactions: a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; b) S. Aoki, K. Mikami, M. Terada, T. Nakai, Tetrahedron 1993, 49, 1783-1792; c) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001 -7002; d) G. E. Keck, K. H. Tarbet, L. S. Geraci, ibid. 1993, 115, 8467-8468; e) G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544; f) S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 1995, 6, 2571-2574; g) D. R. Gauthier, Jr. E. M. Carreira, Angew. Chem. 1996, 108, 2521-2523; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365; h) C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
26. Titanium(IV)-1,1′-bi-2-naphthol complexes were used in some asymmetric reactions: a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; b) S. Aoki, K. Mikami, M. Terada, T. Nakai, Tetrahedron 1993, 49, 1783-1792; c) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001 -7002; d) G. E. Keck, K. H. Tarbet, L. S. Geraci, ibid. 1993, 115, 8467-8468; e) G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544; f) S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 1995, 6, 2571-2574; g) D. R. Gauthier, Jr. E. M. Carreira, Angew. Chem. 1996, 108, 2521-2523; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365; h) C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
27. Titanium(IV)-1,1′-bi-2-naphthol complexes were used in some asymmetric reactions: a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; b) S. Aoki, K. Mikami, M. Terada, T. Nakai, Tetrahedron 1993, 49, 1783-1792; c) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001 -7002; d) G. E. Keck, K. H. Tarbet, L. S. Geraci, ibid. 1993, 115, 8467-8468; e) G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544; f) S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 1995, 6, 2571-2574; g) D. R. Gauthier, Jr. E. M. Carreira, Angew. Chem. 1996, 108, 2521-2523; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365; h) C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
28. Titanium(IV)-1,1′-bi-2-naphthol complexes were used in some asymmetric reactions: a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; b) S. Aoki, K. Mikami, M. Terada, T. Nakai, Tetrahedron 1993, 49, 1783-1792; c) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001 -7002; d) G. E. Keck, K. H. Tarbet, L. S. Geraci, ibid. 1993, 115, 8467-8468; e) G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544; f) S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 1995, 6, 2571-2574; g) D. R. Gauthier, Jr. E. M. Carreira, Angew. Chem. 1996, 108, 2521-2523; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365; h) C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
29. Titanium(IV)-1,1′-bi-2-naphthol complexes were used in some asymmetric reactions: a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; b) S. Aoki, K. Mikami, M. Terada, T. Nakai, Tetrahedron 1993, 49, 1783-1792; c) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001 -7002; d) G. E. Keck, K. H. Tarbet, L. S. Geraci, ibid. 1993, 115, 8467-8468; e) G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544; f) S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 1995, 6, 2571-2574; g) D. R. Gauthier, Jr. E. M. Carreira, Angew. Chem. 1996, 108, 2521-2523; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365; h) C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
30. Titanium(IV)-1,1′-bi-2-naphthol complexes were used in some asymmetric reactions: a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; b) S. Aoki, K. Mikami, M. Terada, T. Nakai, Tetrahedron 1993, 49, 1783-1792; c) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001 -7002; d) G. E. Keck, K. H. Tarbet, L. S. Geraci, ibid. 1993, 115, 8467-8468; e) G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544; f) S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 1995, 6, 2571-2574; g) D. R. Gauthier, Jr. E. M. Carreira, Angew. Chem. 1996, 108, 2521-2523; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365; h) C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
31. Titanium(IV)-1,1′-bi-2-naphthol complexes were used in some asymmetric reactions: a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; b) S. Aoki, K. Mikami, M. Terada, T. Nakai, Tetrahedron 1993, 49, 1783-1792; c) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001 -7002; d) G. E. Keck, K. H. Tarbet, L. S. Geraci, ibid. 1993, 115, 8467-8468; e) G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544; f) S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 1995, 6, 2571-2574; g) D. R. Gauthier, Jr. E. M. Carreira, Angew. Chem. 1996, 108, 2521-2523; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365; h) C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
32. Titanium(IV)-1,1′-bi-2-naphthol complexes were used in some asymmetric reactions: a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; b) S. Aoki, K. Mikami, M. Terada, T. Nakai, Tetrahedron 1993, 49, 1783-1792; c) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001 -7002; d) G. E. Keck, K. H. Tarbet, L. S. Geraci, ibid. 1993, 115, 8467-8468; e) G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544; f) S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 1995, 6, 2571-2574; g) D. R. Gauthier, Jr. E. M. Carreira, Angew. Chem. 1996, 108, 2521-2523; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365; h) C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
33. Titanium(IV)-1,1′-bi-2-naphthol complexes were used in some asymmetric reactions: a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824; b) S. Aoki, K. Mikami, M. Terada, T. Nakai, Tetrahedron 1993, 49, 1783-1792; c) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001 -7002; d) G. E. Keck, K. H. Tarbet, L. S. Geraci, ibid. 1993, 115, 8467-8468; e) G. E. Keck, D. Krishnamurthy, M. C. Grier, J. Org. Chem. 1993, 58, 6543-6544; f) S. Matsukawa, K. Mikami, Tetrahedron: Asymmetry 1995, 6, 2571-2574; g) D. R. Gauthier, Jr. E. M. Carreira, Angew. Chem. 1996, 108, 2521-2523; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365; h) C.-M. Yu, H.-S. Choi, W.-H. Jung, S.-S. Lee, Tetrahedron Lett. 1996, 37, 7095-7098.
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