Domino "[3+3]-cyclization-homo-Michael" reactions of 1,3-bissilyl enol ethers with 1,1-diacylcyclopropanes

Journal of Organic Chemistry

Volumn 69, Issue 26, 2004, Pages 9128-9134

  Bose, Gopal ^a   Nguyen, Van Thi Hong ^a   Ullah, Ehsan ^a   Lahiri, Sunanda ^a   Görls, Helmar ^b   Langer, Peter ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL POLYMERS; ORGANIC ACIDS; PROPANE; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DOMINO PROCESS; LEWIS ACID; SALICYLATES; SUBSTITUTION PATTERNS;

ETHERS;

CYCLOPROPANE DERIVATIVE; ETHER DERIVATIVE; LEWIS ACID; SALICYLIC ACID DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CYCLIZATION; HALOGENATION; MATERIALS; MICHAEL ADDITION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 10844243944     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0485278     Document Type: Article

References (34)

1. For a review of 1,3-bissilyl enol ethers, see: Langer, P. Synthesis 2002, 441.
2. (a) Chan, T.-H.; Brownbridge, P. J. Chem. Soc., Chem. Commun. 1979, 578.
3. (b) Chan, T.-H.; Brownbridge, P. J. Am. Chem. Soc. 1980, 102, 3534.
4. (c) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830.
5. (d) Chan, T. H.; Chaly, T. Tetrahedron Lett. 1982, 23, 2935.
6. (e) Brownbridge, P.; Chan, T.-H.; Brook, M. A.; Kang, G. J. Can. J. Chem. 1983, 61, 688.
7. Reviews: (a) Jorgensen, K. A. Angew. Chem. 2000, 112, 3702; Angew. Chem., Int. Ed. Engl. 2000, 39, 3558.
8. Reviews: (a) Jorgensen, K. A. Angew. Chem. 2000, 112, 3702; Angew. Chem., Int. Ed. Engl. 2000, 39, 3558.
9. (b) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem. 1996, 108, 1482; Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
10. (b) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem. 1996, 108, 1482; Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
11. (c) Bednarski, M. D.; Lyssikatos, J. P. Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, p 661.
12. Langer, P.; Bose, G. Angew. Chem. 2003, 115, 4165; Angew. Chem., Int. Ed. 2003, 42, 4033.
13. Langer, P.; Bose, G. Angew. Chem. 2003, 115, 4165; Angew. Chem., Int. Ed. 2003, 42, 4033.
14. For reviews of domino reactions, see: (a) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
15. For reviews of domino reactions, see: (a) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
16. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
17. The starting materials were prepared according to a known procedure: Zefirov, N. S.; Kuznetsova, T. S.; Kozhushkov, S. I.; Surmina, L. S.; Rakina, Z. A. Zh. Org. Khim. 1983, 19, 541.
18. Bose, G.; Langer, P. Tetrahedron Lett. 2004, 3861.
19. (a) Houben-Weyl, Methoden der Organischen Chemie, 4th ed.; Carbocyclic Three-Membered Ring Compounds, Vol. E17; de Meijere, A., Ed.; Thieme: Stuttgart, Germany, 1996.
20. (b) The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, UK, 1987.
21. Danishefsky, S. J. Acc. Chem. Bes. 1979, 12, 6.
22. Dynamic spiro activation: Zefirov, N. S.; Kozhushkov, S. I.; Kuznetsova, T. S. Tetrahedron 1982, 38, 1693.
23. (a) McMorris, T. C.; Voeller, B. Phytochemistry 1971, 10, 3253.
24. (b) Yoshishira, K.; Fukuoka, M.; Kuroyanagi, M.; Natori, S. Chem. Pharm. Bull. 1971, 19, 1491.
25. (c) Bardouille, V.; Mootoo, B. S.; Hirotsu, K.; Clardy, J. Phytochemistry 1978, 17, 275.
26. (d) Sengupta, P.; Sen, M.; Niyogi, S. K.; Pakrashi, S. C.; Ali, E. Phytochemistry 1976, 15, 995.
27. (e) Yoshihira, K.; Fukuoka, M.; Kuroyanagi, M.; Natori, S.; Umeda, M.; Morohoshi, T.; Enomoto, M.; Saito, M. Chem. Pharm. Bull. 1978, 26, 2346.
28. (a) McMorris, T. C.; Anchel, M. J. Am. Chem. Soc. 1985, 87, 1594.
29. (b) McMorris, T. C.; Kelner, M. J.; Wang, W.; Estes, L. A.; Montoya, M. A.; Taetle, R. J. Org. Chem. 1992, 57, 6876 and references therein.
30. Padwa, A.; Curtis, E. A.; Sandanayaka, V. P. J. Org. Chem. 1996, 61, 73 and references therein.
31. COLLECT; Data Collection Software: Nonius B.V., The Netherlands, 1998.
32. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Methods in Enzymology; Vol. 276, Macromolecular Crystallography, Part A; Carter, C. W., Sweet, R. M., Eds.; Academic Press: New York, 1997; pp 307-326.
33. Sheldrick, G. M. Acta Crystallogr. Sect. A 1980, 46, 467-473.
34. Sheldrick, G. M. SHELXL-97, Release 97-2; University of Göttingen: Göttingen, Germany, 1997.