Asymmetric hetero Diels-Alder reaction of homochiral thiabutadienes, 3-(arylmethylene)thiocamphors

Tetrahedron Letters

Volumn 40, Issue 48, 1999, Pages 8383-8386

  Saito, Takao ^a   Nishimura, Junichi ^a   Akiba, Daisuke ^a   Kusuoku, Hiroshi ^a   Kobayashi, Kimiko ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Asymmetric synthesis; Diels Alder reactions; Thiocarbonyl compounds; Thiopyrans

Indexed keywords

1,3 BUTADIENE DERIVATIVE; CAMPHOR DERIVATIVE; CARBONYL DERIVATIVE; THIOPYRAN DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; OPTICAL ROTATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033607436     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01746-3     Document Type: Article

References (27)

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2. Asymmetric Synthesis; Morrison, J. D., Ed.; 1983; Vol. 2, and 1985; Vol. 5; Money, T. Natural Prod. Reports 1985, 253; Oppolzer, W. Tetrahedron 1987, 43, 1969; Blaser, H.-U. Chem. Rev. 1992, 92, 935; Arai, Y.; Koizumi, T. Sulfur Reports 1993, 15, 41.
3. Asymmetric Synthesis; Morrison, J. D., Ed.; 1983; Vol. 2, and 1985; Vol. 5; Money, T. Natural Prod. Reports 1985, 253; Oppolzer, W. Tetrahedron 1987, 43, 1969; Blaser, H.-U. Chem. Rev. 1992, 92, 935; Arai, Y.; Koizumi, T. Sulfur Reports 1993, 15, 41.
4. Asymmetric Synthesis; Morrison, J. D., Ed.; 1983; Vol. 2, and 1985; Vol. 5; Money, T. Natural Prod. Reports 1985, 253; Oppolzer, W. Tetrahedron 1987, 43, 1969; Blaser, H.-U. Chem. Rev. 1992, 92, 935; Arai, Y.; Koizumi, T. Sulfur Reports 1993, 15, 41.
5. Asymmetric Synthesis; Morrison, J. D., Ed.; 1983; Vol. 2, and 1985; Vol. 5; Money, T. Natural Prod. Reports 1985, 253; Oppolzer, W. Tetrahedron 1987, 43, 1969; Blaser, H.-U. Chem. Rev. 1992, 92, 935; Arai, Y.; Koizumi, T. Sulfur Reports 1993, 15, 41.
6. Asymmetric Synthesis; Morrison, J. D., Ed.; 1983; Vol. 2, and 1985; Vol. 5; Money, T. Natural Prod. Reports 1985, 253; Oppolzer, W. Tetrahedron 1987, 43, 1969; Blaser, H.-U. Chem. Rev. 1992, 92, 935; Arai, Y.; Koizumi, T. Sulfur Reports 1993, 15, 41.
7. Asymmetric Synthesis; Morrison, J. D., Ed.; 1983; Vol. 2, and 1985; Vol. 5; Money, T. Natural Prod. Reports 1985, 253; Oppolzer, W. Tetrahedron 1987, 43, 1969; Blaser, H.-U. Chem. Rev. 1992, 92, 935; Arai, Y.; Koizumi, T. Sulfur Reports 1993, 15, 41.
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10. For recent literatures, see: Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.;Percàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037; Morris, D. G.; Ryder, K. S. Synthesis 1997, 620; Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1996, 7, 1269; de Vries, A. H. M.; Imbos, R.; Feringa, B. L. Tetrahedron:asymmetry 1997, 8, 1467; Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans, 1 1993, 153.
11. For recent literatures, see: Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.;Percàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037; Morris, D. G.; Ryder, K. S. Synthesis 1997, 620; Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1996, 7, 1269; de Vries, A. H. M.; Imbos, R.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 1467; Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans, 1 1993, 153.
12. For recent literatures, see: Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.;Percàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037; Morris, D. G.; Ryder, K. S. Synthesis 1997, 620; Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1996, 7, 1269; de Vries, A. H. M.; Imbos, R.; Feringa, B. L. Tetrahedron:asymmetry 1997, 8, 1467; Tanaka, K.; Matsui, J.; Suzuki, H. J. Chem. Soc., Perkin Trans, 1 1993, 153.
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14. Motoki, S.; Saito, T.; Karakasa, T.; Kato, H.; Matsushita, T.; Hayashibe, S. J. Chem. Soc., Perkin Trans. 1 1991, 2281; Saito, T.; Fujii, H.; Hayashibe, S.; Matsushita, T.; Kato, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1996, 1897; Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1359; Saito, T.; Kawamura, M.; Nishimura, J. Tetrahedron Lett. 1997, 38, 3231; Saito, T.; Suda, H.; Kawamura, M.; Nishimura, J.;Yamaya, A. Tetrahedron Lett. 1997, 38, 6035; Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957; Saito, T.; Takekawa, K.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1999, 1001.
15. Motoki, S.; Saito, T.; Karakasa, T.; Kato, H.; Matsushita, T.; Hayashibe, S. J. Chem. Soc., Perkin Trans. 1 1991, 2281; Saito, T.; Fujii, H.; Hayashibe, S.; Matsushita, T.; Kato, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1996, 1897; Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1359; Saito, T.; Kawamura, M.; Nishimura, J. Tetrahedron Lett. 1997, 38, 3231; Saito, T.; Suda, H.; Kawamura, M.; Nishimura, J.;Yamaya, A. Tetrahedron Lett. 1997, 38, 6035; Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957; Saito, T.; Takekawa, K.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1999, 1001.
16. Motoki, S.; Saito, T.; Karakasa, T.; Kato, H.; Matsushita, T.; Hayashibe, S. J. Chem. Soc., Perkin Trans. 1 1991, 2281; Saito, T.; Fujii, H.; Hayashibe, S.; Matsushita, T.; Kato, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1996, 1897; Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1359; Saito, T.; Kawamura, M.; Nishimura, J. Tetrahedron Lett. 1997, 38, 3231; Saito, T.; Suda, H.; Kawamura, M.; Nishimura, J.;Yamaya, A. Tetrahedron Lett. 1997, 38, 6035; Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957; Saito, T.; Takekawa, K.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1999, 1001.
17. Motoki, S.; Saito, T.; Karakasa, T.; Kato, H.; Matsushita, T.; Hayashibe, S. J. Chem. Soc., Perkin Trans. 1 1991, 2281; Saito, T.; Fujii, H.; Hayashibe, S.; Matsushita, T.; Kato, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1996, 1897; Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1359; Saito, T.; Kawamura, M.; Nishimura, J. Tetrahedron Lett. 1997, 38, 3231; Saito, T.; Suda, H.; Kawamura, M.; Nishimura, J.; Yamaya, A. Tetrahedron Lett. 1997, 38, 6035; Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957; Saito, T.; Takekawa, K.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1999, 1001.
18. Motoki, S.; Saito, T.; Karakasa, T.; Kato, H.; Matsushita, T.; Hayashibe, S. J. Chem. Soc., Perkin Trans. 1 1991, 2281; Saito, T.; Fujii, H.; Hayashibe, S.; Matsushita, T.; Kato, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1996, 1897; Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1359; Saito, T.; Kawamura, M.; Nishimura, J. Tetrahedron Lett. 1997, 38, 3231; Saito, T.; Suda, H.; Kawamura, M.; Nishimura, J.;Yamaya, A. Tetrahedron Lett. 1997, 38, 6035; Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957; Saito, T.; Takekawa, K.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1999, 1001.
19. Motoki, S.; Saito, T.; Karakasa, T.; Kato, H.; Matsushita, T.; Hayashibe, S. J. Chem. Soc., Perkin Trans. 1 1991, 2281; Saito, T.; Fujii, H.; Hayashibe, S.; Matsushita, T.; Kato, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1996, 1897; Saito, T.; Karakasa, T.; Fujii, H.; Furuno, E.; Suda, H.; Kobayashi, K. J. Chem. Soc., Perkin Trans. 1 1994, 1359; Saito, T.; Kawamura, M.; Nishimura, J. Tetrahedron Lett. 1997, 38, 3231; Saito, T.; Suda, H.; Kawamura, M.; Nishimura, J.;Yamaya, A. Tetrahedron Lett. 1997, 38, 6035; Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957; Saito, T.; Takekawa, K.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1999, 1001.
20. Sen, D. C. J. Indian Chem. Soc. 1936, 13, 523.
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23. 3) 0.76 (3H, s), 0.89 (3H, s), 1.01 (3H, s), 0.88-1.70 (4H, m), 2.10 (1H, d, J=3.3), 2.84 (1H, ddd, J=1.1, 2.6, 13.2), 3.08 (1H, ddd, J=2.6, 4.8, 12.5), 3.17 (1H, dd, J=12.5, 13.2), 3.51 (3H, s), 4.01 (1H, d, J=4.8), 7.02-7.04 (2H, m), 7.19-7.26 (3H, m).
24. 0/). Final R and Rw values are 0.045 and 0.048, respectively.
25. The cycloadducts can be used as useful chiral compounds by further manipulation, e.g., as a chiral sulfide catalyst in asymmetric epoxidation and aziridination (for reviews, see: Aggawal, V. K. Synlett 1998, 329; Li, A.-H.; Dai, L.-X.;Aggawal, V. K. Chem. Rev. 1997, 97, 2341). Results regarding this study will be published elsewhere. (Saito, T.; Akiba, D.; Kanazawa, S. presented at the 76th Annual Meeting of the Chemical Society of Japan, Yokohama, 1999, Vol. II, p.810).
26. The cycloadducts can be used as useful chiral compounds by further manipulation, e.g., as a chiral sulfide catalyst inasymmetric epoxidation and aziridination (for reviews, see: Aggawal, V. K. Synlett 1998, 329; Li, A.-H.; Dai, L.-X.; Aggawal, V. K. Chem. Rev. 1997, 97, 2341). Results regarding this study will be published elsewhere. (Saito, T.; Akiba, D.; Kanazawa, S. presented at the 76th Annual Meeting of the Chemical Society of Japan, Yokohama, 1999, Vol. II, p.810).
27. The cycloadducts can be used as useful chiral compounds by further manipulation, e.g., as a chiral sulfide catalyst inasymmetric epoxidation and aziridination (for reviews, see: Aggawal, V. K. Synlett 1998, 329; Li, A.-H.; Dai, L.-X.;Aggawal, V. K. Chem. Rev. 1997, 97, 2341). Results regarding this study will be published elsewhere. (Saito, T.; Akiba, D.; Kanazawa, S. presented at the 76th Annual Meeting of the Chemical Society of Japan, Yokohama, 1999, Vol. II, p. 810).