The first catalytic, highly enantioselective hetero-Diels-Alder reaction of thiabutadienes

Chemical Communications

Volumn , Issue 11, 1999, Pages 1001-1002

  Saito, Takao ^a   Takekawa, Kayoko ^a   Takahashi, Tatsuhisa ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; COPPER; DIHYDROTHIOPYRAN; NICKEL; PERCHLORATE; THIABUTADIENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0033532517     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a902076d     Document Type: Article

References (23)

1. L. F. Tietze and G. Kettshau, Top. Curr. Chem., 1997, 189, 1; S. Laschat, Liebigs Ann. Chem., 1997, 1; H. Waldmann, Synthesis, 1994, 535; P. F. Vogt and M. J. Miller, Tetrahedron, 1998, 54, 1317; J. Streith and A. Defoin, Synthesis, 1994, 1107; C. Kibayashi and S. Aoyagi, Synlett, 1995, 873 and references cited therein and in ref. 4.
2. L. F. Tietze and G. Kettshau, Top. Curr. Chem., 1997, 189, 1; S. Laschat, Liebigs Ann. Chem., 1997, 1; H. Waldmann, Synthesis, 1994, 535; P. F. Vogt and M. J. Miller, Tetrahedron, 1998, 54, 1317; J. Streith and A. Defoin, Synthesis, 1994, 1107; C. Kibayashi and S. Aoyagi, Synlett, 1995, 873 and references cited therein and in ref. 4.
3. L. F. Tietze and G. Kettshau, Top. Curr. Chem., 1997, 189, 1; S. Laschat, Liebigs Ann. Chem., 1997, 1; H. Waldmann, Synthesis, 1994, 535; P. F. Vogt and M. J. Miller, Tetrahedron, 1998, 54, 1317; J. Streith and A. Defoin, Synthesis, 1994, 1107; C. Kibayashi and S. Aoyagi, Synlett, 1995, 873 and references cited therein and in ref. 4.
4. L. F. Tietze and G. Kettshau, Top. Curr. Chem., 1997, 189, 1; S. Laschat, Liebigs Ann. Chem., 1997, 1; H. Waldmann, Synthesis, 1994, 535; P. F. Vogt and M. J. Miller, Tetrahedron, 1998, 54, 1317; J. Streith and A. Defoin, Synthesis, 1994, 1107; C. Kibayashi and S. Aoyagi, Synlett, 1995, 873 and references cited therein and in ref. 4.
5. L. F. Tietze and G. Kettshau, Top. Curr. Chem., 1997, 189, 1; S. Laschat, Liebigs Ann. Chem., 1997, 1; H. Waldmann, Synthesis, 1994, 535; P. F. Vogt and M. J. Miller, Tetrahedron, 1998, 54, 1317; J. Streith and A. Defoin, Synthesis, 1994, 1107; C. Kibayashi and S. Aoyagi, Synlett, 1995, 873 and references cited therein and in ref. 4.
6. L. F. Tietze and G. Kettshau, Top. Curr. Chem., 1997, 189, 1; S. Laschat, Liebigs Ann. Chem., 1997, 1; H. Waldmann, Synthesis, 1994, 535; P. F. Vogt and M. J. Miller, Tetrahedron, 1998, 54, 1317; J. Streith and A. Defoin, Synthesis, 1994, 1107; C. Kibayashi and S. Aoyagi, Synlett, 1995, 873 and references cited therein and in ref. 4.
7. For asymmetric hetero-Diels-Alder reaction with thiocarbonyl dienophiles: E. Vedjes, J. S. Stults and R. G. Wilde, J. Am. Chem. Soc., 1988, 110, 5452; G. W. Kirby and A. D. Sclare, J. Chem. Soc., Perkin Trans. 1, 1991, 2329; B. F. Bonini, G. Mazzanti, P. Zani and G. Maccagnani, J. Chem. Soc., Chem. Commun., 1988, 365; T. Takahashi, N. Kurose and T. Koizumi, Heterocycles, 1993, 36, 1601.
8. For asymmetric hetero-Diels-Alder reaction with thiocarbonyl dienophiles: E. Vedjes, J. S. Stults and R. G. Wilde, J. Am. Chem. Soc., 1988, 110, 5452; G. W. Kirby and A. D. Sclare, J. Chem. Soc., Perkin Trans. 1, 1991, 2329; B. F. Bonini, G. Mazzanti, P. Zani and G. Maccagnani, J. Chem. Soc., Chem. Commun., 1988, 365; T. Takahashi, N. Kurose and T. Koizumi, Heterocycles, 1993, 36, 1601.
9. For asymmetric hetero-Diels-Alder reaction with thiocarbonyl dienophiles: E. Vedjes, J. S. Stults and R. G. Wilde, J. Am. Chem. Soc., 1988, 110, 5452; G. W. Kirby and A. D. Sclare, J. Chem. Soc., Perkin Trans. 1, 1991, 2329; B. F. Bonini, G. Mazzanti, P. Zani and G. Maccagnani, J. Chem. Soc., Chem. Commun., 1988, 365; T. Takahashi, N. Kurose and T. Koizumi, Heterocycles, 1993, 36, 1601.
10. For asymmetric hetero-Diels-Alder reaction with thiocarbonyl dienophiles: E. Vedjes, J. S. Stults and R. G. Wilde, J. Am. Chem. Soc., 1988, 110, 5452; G. W. Kirby and A. D. Sclare, J. Chem. Soc., Perkin Trans. 1, 1991, 2329; B. F. Bonini, G. Mazzanti, P. Zani and G. Maccagnani, J. Chem. Soc., Chem. Commun., 1988, 365; T. Takahashi, N. Kurose and T. Koizumi, Heterocycles, 1993, 36, 1601.
11. For asymmetric hetero-Diels-Alder reaction with thiabutadienes: (a) S. Motoki, T. Saito, T. Karakasa, H. Kato, T. Matsushita and S. Hayashibe, J. Chem. Soc., Perkin Trans. 1, 1991, 2281;
12. (b) T. Saito, H. Fujii, S. Hayashibe, T. Matsushita, H. Kato and K. Kobayashi, J. Chem. Soc., Perkin Trans. 1, 1996, 1897;
13. (c) T. Saito, T. Karakasa, H. Fujii, E. Furuno, H. Suda and K. Kobayashi, J. Chem. Soc., Perkin Trans. 1, 1994, 1359;
14. (d) T. Saito, M. Kawamura and J. Nishimura, Tetrahedron Lett., 1997, 38, 3231;
15. (e) T. Saito, H. Suda, M. Kawamura, J. Nishimura and A. Yamaya, Tetrahedron Lett., 1997, 38, 6035;
16. (f) A. Marchand, D. Mauger, A. Guingant and J.-P. Pradère, Tetrahedron: Asymmetry, 1995, 6, 853;
17. (g) A. S. Bell, C. W. G. Fishwick and J. E. Reed, Tetrahedron, 1998, 54, 3219.
18. T. Saito, K. Takekawa, J. Nishimura and M. Kawamura, J. Chem. Soc., Perkin Trans. 1, 1997, 2957.
19. A. K. Ghosh, P. Mathivanan and J. Cappiello, Tetrahedron Lett., 1996, 37, 3815; A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165. See also I. W. Davies, C. K. Senanayake, R. D. Larsen, T. R. Verhoeven and P. J. Reider, Tetrahedron Lett., 1996, 37, 1725.
20. A. K. Ghosh, P. Mathivanan and J. Cappiello, Tetrahedron Lett., 1996, 37, 3815; A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165. See also I. W. Davies, C. K. Senanayake, R. D. Larsen, T. R. Verhoeven and P. J. Reider, Tetrahedron Lett., 1996, 37, 1725.
21. A. K. Ghosh, P. Mathivanan and J. Cappiello, Tetrahedron Lett., 1996, 37, 3815; A. K. Ghosh, P. Mathivanan, J. Cappiello and K. Krishnan, Tetrahedron: Asymmetry, 1996, 7, 2165. See also I. W. Davies, C. K. Senanayake, R. D. Larsen, T. R. Verhoeven and P. J. Reider, Tetrahedron Lett., 1996, 37, 1725.
22. A. K. Ghosh, P. Mathivanan and J. Cappiello, Tetrahedron: Asymmetry, 1998, 9, 1.
23. K. V. Gothelf, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 1998, 63, 5483 and references cited therein.