Radical-Induced Cyclizations of 1-Sila-cyclopent-2-ene Derivatives: Synthesis of Novel Azasilabicyclic Compounds

Synlett

Volumn 1996, Issue 9, 1996, Pages 890-892

  Damour, Dominique ^a   Barreau, Michel ^a   Dhaleine, Fabrice ^a   Doerflinger, Gilles ^a   Vuilhorgne, Marc ^a   Mignani, Serge ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0242414429     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5586     Document Type: Article

References (32)

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2. For reviews, see: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Eds: Pergamon Press, Oxford, 1986; Curran, D. P. Synthesis 1988, 417; Curran, D. P. Synthesis 1988 489; Regitz, M.; Giese, B. Houben-Weyl, Eds Methoden der Organischen Chemie, C-Radikale, Stuttgart, 1989, Vol. E19A; Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 296; Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, Concepts, Guidelines, and Synthetic Applications, Eds VCH, Weinheim, 1995 and references cited therein.
3. For reviews, see: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Eds: Pergamon Press, Oxford, 1986; Curran, D. P. Synthesis 1988, 417; Curran, D. P. Synthesis 1988 489; Regitz, M.; Giese, B. Houben-Weyl, Eds Methoden der Organischen Chemie, C-Radikale, Stuttgart, 1989, Vol. E19A; Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 296; Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, Concepts, Guidelines, and Synthetic Applications, Eds VCH, Weinheim, 1995 and references cited therein.
4. For reviews, see: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Eds: Pergamon Press, Oxford, 1986; Curran, D. P. Synthesis 1988, 417; Curran, D. P. Synthesis 1988 489; Regitz, M.; Giese, B. Houben-Weyl, Eds Methoden der Organischen Chemie, C-Radikale, Stuttgart, 1989, Vol. E19A; Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 296; Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, Concepts, Guidelines, and Synthetic Applications, Eds VCH, Weinheim, 1995 and references cited therein.
5. For reviews, see: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Eds: Pergamon Press, Oxford, 1986; Curran, D. P. Synthesis 1988, 417; Curran, D. P. Synthesis 1988 489; Regitz, M.; Giese, B. Houben-Weyl, Eds Methoden der Organischen Chemie, C-Radikale, Stuttgart, 1989, Vol. E19A; Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 296; Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, Concepts, Guidelines, and Synthetic Applications, Eds VCH, Weinheim, 1995 and references cited therein.
6. For reviews, see: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Eds: Pergamon Press, Oxford, 1986; Curran, D. P. Synthesis 1988, 417; Curran, D. P. Synthesis 1988 489; Regitz, M.; Giese, B. Houben-Weyl, Eds Methoden der Organischen Chemie, C-Radikale, Stuttgart, 1989, Vol. E19A; Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 296; Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, Concepts, Guidelines, and Synthetic Applications, Eds VCH, Weinheim, 1995 and references cited therein.
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11. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
12. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
13. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
14. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
15. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
16. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
17. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
18. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
19. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
20. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
21. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
22. Stork, G.; Sher, P.; Chen, H-L. J. Am. Chem. Soc. 1986, 108, 6384; Dener, J. M.; Hart, D. Tetrahedron 1988, 44, 7037; Lee, E.; Yu, S-G., Hur, C-G.; Yang, S-M. Tetrahedron Lett. 1988, 29, 769; Toru, T.; Seko, T.; Maekawa, E.; Ueno, E. J. Chem.Soc. Perkin Trans I 1989, 1, 1927; Renaud, P. Tetrahedron Lett. 1990, 31, 769. Burke, S. D.; Rancourt, J. J. Am. Chem. Soc. 1991, 113, 113, 2335; Boiteau, L. Thesis (Dr. S. Zard, Ecole Polytechnique, Palaiseau, France), 1994; Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron 1990, 48, 2613; Burke, S. D.; Jung, K. W. Tetrahedron Lett. 1994, 35, 5837; Renaud, P.; Gester, M.; Ribezzo, M. Chimia 1994, 48, 366; Altamura, M.; Giammaruco, M.; Taddei, M.; Ulivi, P. J. Org. Chem. 1995, 60, 8403; Kashimura, S.; Ishifune, M.; Murai, Y.; Moriyoshi, N.; Shono, T. Tetrahedron Lett. 1995, 36, 769, Vaupel, A.; Knochel, P. Tetrahedron Lett., 1995, 36, 231.
23. 31NSi, HCl: C, 77.22; H, 6.69; Cl, 7.35; N, 2.91; Si, 5.83. Found (1.0% water): C. 76.6; H, 7.1; Cl, 7.1; N, 3.2; Si, 7.
24. 3 on a AC250 Bruker spectrometer for compounds 13 (base form) and 19, and on a AM400 Bruker spectrometer for compound 27 (base form).
25. 1,1-Diphenyl-1-sila-cyclopent-3-ene 5 was prepared on large scale according to our previously described procedure (Mignani, S.; Damour, D.; Bastart, J.-P.; Manuel, G. Synth. Commun. 1995, 25, 3855).
26. Ene reactions between 1-sila-cyclopent-3-ene derivatives and diethyl azodicarboxylate have been previously described: Laporterie, A.; Dubac, J.; Lesbre, M. J. Organomet. Chem. 1975, 101, 187; Lesbre, M.; Laporterie, A.; Dubac, J.; Manuel, G. C R. Hebd. Sceances Acad. Sci. Ser. C 1975, 280, 787; Laporterie, A.; Dubac, Manuel, G.; Deleris, G.; Kowalski, J.; Dunogues, J.; Calas, R. Tetrahedron 1978, 34, 2669.
27. Ene reactions between 1-sila-cyclopent-3-ene derivatives and diethyl azodicarboxylate have been previously described: Laporterie, A.; Dubac, J.; Lesbre, M. J. Organomet. Chem. 1975, 101, 187; Lesbre, M.; Laporterie, A.; Dubac, J.; Manuel, G. C R. Hebd. Sceances Acad. Sci. Ser. C 1975, 280, 787; Laporterie, A.; Dubac, Manuel, G.; Deleris, G.; Kowalski, J.; Dunogues, J.; Calas, R. Tetrahedron 1978, 34, 2669.
28. Ene reactions between 1-sila-cyclopent-3-ene derivatives and diethyl azodicarboxylate have been previously described: Laporterie, A.; Dubac, J.; Lesbre, M. J. Organomet. Chem. 1975, 101, 187; Lesbre, M.; Laporterie, A.; Dubac, J.; Manuel, G. C R. Hebd. Sceances Acad. Sci. Ser. C 1975, 280, 787; Laporterie, A.; Dubac, Manuel, G.; Deleris, G.; Kowalski, J.; Dunogues, J.; Calas, R. Tetrahedron 1978, 34, 2669.
29. Salomon, M. F.; Pardo, S. N.; Salomon, R. G. J. Am. Chem. Soc. 1984, 106, 3797 and references cited therein.
30. Salomon, R.G.; Roy, S.; Salomon, M. F. Tetrahedron Lett., 1988, 769.
31. 3SnH; see: Kuivila, H. G. Synthesis 1970, 499 and references cited therein.
32. Lee, S.; Frescas, S. P.; Nichols, D. E. Synth. Commun 1995, 25, 2775.