Asymmetric Cyclopentannulation of Cyclic Enones with a Chiral 1,3-Dipole Equivalent

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 6, 1997, Pages 634-636

  Huart, Catherine ^a   Ghosez, Léon ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Asymmetric synthesis; Carbanions; Cyclizations; Cyclopentenones; Sulfonamides

Indexed keywords

EID: 0030948204     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199706341     Document Type: Article

References (30)

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2. Reviews: M. Ramaiah, Synthesis 1984, 529; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; T. Hudlicky, J. D. Price, Chem. Rev. 1989, 89, 1467; M. E. Welker, ibid. 1992, 92, 97.
3. Reviews: M. Ramaiah, Synthesis 1984, 529; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; T. Hudlicky, J. D. Price, Chem. Rev. 1989, 89, 1467; M. E. Welker, ibid. 1992, 92, 97.
4. Reviews: M. Ramaiah, Synthesis 1984, 529; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; T. Hudlicky, J. D. Price, Chem. Rev. 1989, 89, 1467; M. E. Welker, ibid. 1992, 92, 97.
5. Reviews: M. Ramaiah, Synthesis 1984, 529; B. M. Trost, Angew. Chem. 1986, 98, 1; Angew. Chem. Int. Ed. Engl. 1986, 25, 1; T. Hudlicky, J. D. Price, Chem. Rev. 1989, 89, 1467; M. E. Welker, ibid. 1992, 92, 97.
6. Best results can be found in the following papers: Trost's annulation: M. Malacria, F. Chaigne, J. P. Gotteleand, Tetrahedron Lett. 1989, 30, 1803; B. M. Trost, P. Scoane, S. Mignani, M. Acemoglu, J. Am. Chem. Soc. 1989, 111, 7487; M. Janson, I. Kvarnstrom, S. C. T. Svensson, B. Classon, B. Samuelsson, Synthesis 1993, 129; methylenecyclopropanes: P. Binger, A. Brinkmann, W. J. Richter, Tetrahedron Lett. 1983, 24, 3599;
7. Best results can be found in the following papers: Trost's annulation: M. Malacria, F. Chaigne, J. P. Gotteleand, Tetrahedron Lett. 1989, 30, 1803; B. M. Trost, P. Scoane, S. Mignani, M. Acemoglu, J. Am. Chem. Soc. 1989, 111, 7487; M. Janson, I. Kvarnstrom, S. C. T. Svensson, B. Classon, B. Samuelsson, Synthesis 1993, 129; methylenecyclopropanes: P. Binger, A. Brinkmann, W. J. Richter, Tetrahedron Lett. 1983, 24, 3599;
8. Best results can be found in the following papers: Trost's annulation: M. Malacria, F. Chaigne, J. P. Gotteleand, Tetrahedron Lett. 1989, 30, 1803; B. M. Trost, P. Scoane, S. Mignani, M. Acemoglu, J. Am. Chem. Soc. 1989, 111, 7487; M. Janson, I. Kvarnstrom, S. C. T. Svensson, B. Classon, B. Samuelsson, Synthesis 1993, 129; methylenecyclopropanes: P. Binger, A. Brinkmann, W. J. Richter, Tetrahedron Lett. 1983, 24, 3599;
9. Best results can be found in the following papers: Trost's annulation: M. Malacria, F. Chaigne, J. P. Gotteleand, Tetrahedron Lett. 1989, 30, 1803; B. M. Trost, P. Scoane, S. Mignani, M. Acemoglu, J. Am. Chem. Soc. 1989, 111, 7487; M. Janson, I. Kvarnstrom, S. C. T. Svensson, B. Classon, B. Samuelsson, Synthesis 1993, 129; methylenecyclopropanes: P. Binger, A. Brinkmann, W. J. Richter, Tetrahedron Lett. 1983, 24, 3599;
10. P. Binger, B. Schäfer, ibid. 1988, 29, 529;
11. Meyer's lactams: S. Bienz, C. Busacca, A. I. Meyers, J. Am. Chem. Soc. 1989, 111, 1905;
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13. see also M. Hatanaka, Y. Tanaka, I. Veda, Tetrahedron Lett. 1995, 36, 3719;
14. V. Bernardes, X. Verdaguer, N. Kardos, A. Riera, A. Moyano, M. A. Pericas, A. E. Greene, ibid. 1994, 35, 575;
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22. Allylic sulfoxides: D. H. Hua, S. Venkatamaran, M. J. Coulter, G. Sinal-Zingde, J. Org. Chem. 1987, 52, 719; Trost's annulation: B. M. Trost, D. M. T. Chan, J. Am. Chem. Soc. 1983, 105, 2326; A. Yamamoto, Y. Ito, T. Hayashi, Tetrahedron Lett. 1989, 30, 375; allylsilanes: J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; β-alkoxyacrylates: A. Datta, R. R. Schmidt, Tetrahedron Lett. 1993, 34, 4161.
23. Allylic sulfoxides: D. H. Hua, S. Venkatamaran, M. J. Coulter, G. Sinal-Zingde, J. Org. Chem. 1987, 52, 719; Trost's annulation: B. M. Trost, D. M. T. Chan, J. Am. Chem. Soc. 1983, 105, 2326; A. Yamamoto, Y. Ito, T. Hayashi, Tetrahedron Lett. 1989, 30, 375; allylsilanes: J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; β-alkoxyacrylates: A. Datta, R. R. Schmidt, Tetrahedron Lett. 1993, 34, 4161.
24. Allylic sulfoxides: D. H. Hua, S. Venkatamaran, M. J. Coulter, G. Sinal-Zingde, J. Org. Chem. 1987, 52, 719; Trost's annulation: B. M. Trost, D. M. T. Chan, J. Am. Chem. Soc. 1983, 105, 2326; A. Yamamoto, Y. Ito, T. Hayashi, Tetrahedron Lett. 1989, 30, 375; allylsilanes: J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; β-alkoxyacrylates: A. Datta, R. R. Schmidt, Tetrahedron Lett. 1993, 34, 4161.
25. Allylic sulfoxides: D. H. Hua, S. Venkatamaran, M. J. Coulter, G. Sinal-Zingde, J. Org. Chem. 1987, 52, 719; Trost's annulation: B. M. Trost, D. M. T. Chan, J. Am. Chem. Soc. 1983, 105, 2326; A. Yamamoto, Y. Ito, T. Hayashi, Tetrahedron Lett. 1989, 30, 375; allylsilanes: J. S. Panek, N. F. Jain, J. Org. Chem. 1993, 58, 2345; β-alkoxyacrylates: A. Datta, R. R. Schmidt, Tetrahedron Lett. 1993, 34, 4161.
26. S. De Lombaert, I. Nemery, B. Roekens, J. C. Carretero, T. Kimmel, L. Ghosez, Tetrahedron Lett. 1986, 27, 5099; L. Ghosez, Pure Appl. Chem. 1996, 68, 15.
27. S. De Lombaert, I. Nemery, B. Roekens, J. C. Carretero, T. Kimmel, L. Ghosez, Tetrahedron Lett. 1986, 27, 5099; L. Ghosez, Pure Appl. Chem. 1996, 68, 15.
28. D. Enders, H. Kipphardt, P. Gerdes, L. J. Brena-Valle, V. Bhushan, Bull. Soc. Chim. Belg. 1988, 97, 691.
29. S. Murata, M. Suzuki, R. Noyori, Tetrahedron 1988, 44, 4259.
30. B. Tinant, J. P. Declercq, C. Huart, Acta Crystallogr. Sect. C 1995, 51, 678.