Intermolecular trapping of the Nazarov intermediate: Domino electro- cyclization/[3+2] cycloadditions with allylsilanes

Angewandte Chemie - International Edition

Volumn 39, Issue 11, 2000, Pages 1970-1973

  Giese, Sören ^a   Kastrup, Lars ^a   Stiens, Dirk ^a   West, Frederick G ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Domino reactions; Lewis acids; Polycycles; Silicon organic compounds; Synthetic methods

Indexed keywords

SILANE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; ELECTROCHEMISTRY; MOLECULAR STABILITY; REACTION ANALYSIS;

EID: 0034596074     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000602)39:11<1970::AID-ANIE1970>3.0.CO;2-B     Document Type: Article

References (40)

1. a) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
2. b) N. Hall, Science 1994, 266, 32-34;
3. c) T. L. Ho, Tandem Reactions in Organic Synthesis, Wiley-Interscicnce, New York, 1992.
4. a) T. Hudlicky, Chem. Rev. 1996, 96, 3-30;
5. b) T. Hudlicky, M. G. Natchus in Organic Synthesis: Theory unit Applications, Vol. 2 (Ed.: T. Hudlicky), JAI Press, Greenwich, CT, 1993, pp. 1-26;
6. c) P. A. Wender, B. L. Miller in Organic Synthesis: Theory and Applications, Vol. 2 (Ed.: T. Hudlicky), JAI Press, Greenwich, CT, 1993, pp. 27-66.
7. Reviews: a) K. L. Habermas, S. E. Denmark, T. K. Jones, Org. React. (N.Y.) 1994, 45, 1-158;
8. b) S. E. Denmark in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 751-784.
9. a) J. A. Bender, A. E. Blire, C. C. Browder, S. Giese, F. G. West, J. Org. Chem. 1998, 63, 2430-2431;
10. b) Y. Wang, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 876-877;
11. c) C. C. Browder, F. G. West, Synlett 1999, 1363-1366;
12. d) J. A. Bender, A. M. Arif, F. G. West, J. Am. Chem. Soc. 1999, 121, 7443-7444.
13. S. Giese, F. G. West, Tetrahedron Lett. 1998, 39, 8393-8396.
14. Reviews on allylsilanes: a) I. Fleming, A. Barbero, D. Walter, Chem. Rev. 1997, 97, 2063-2192;
15. b) I. Fleming, J. Dunoguès, R. Smithers, Org. React. (N.Y.) 1989, 37, 57-575.
16. a) M. F. Gotta, H. Mayr, J. Org. Chem. 1998, 63, 9769-9775;
17. b) H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010; Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957.
18. b) H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010; Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957.
19. Recent examples of [3+2] annulations employing allylsilanes: a) H. Monti, D. Rizzotto, G. Léandri, Tetrahedron 1998, 54, 6725-6738;
20. b) H.-J. Knölker, P.G. Jones, G. Wanzl, Synlett 1998, 613-616;
21. c) G. M. Choi, S. H. Yeon, J. Jin, B. R. Yoo, I. N. Jung, Organometallics 1997, 16, 5158-5162;
22. d) W. S. Murphy, D. Neville, Tetrahedron Lett. 1997, 38, 7933-7936;
23. e) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 1997, 3, 538-551;
24. f) R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845-3848;
25. g) R. L. Danheiser, B. R. Dixon, R. W. Gleason, J. Org. Chem. 1992, 57, 6094-6097.
26. Other oxyallyl + alkene [3+2] annulations: a) H. Mizuno, K. Domon, K. Masuya, K. Tunino, I. Kuwajima, J. Org. Chem. 1999, 64, 2648-2656;
27. b) S. A. Hardinger, C. Bayne, E. Kanorowski, R. McClellan, L. Larres, M.-A. Nuesse. J. Org. Chem. 1995, 60, 1104-1105;
28. c) Y. Hayakawa, K. Yokoyama, R. Noyori, J. Am. Hum. Soc. 1978, 100, 1799-1806.
29. a) C. W. Shoppee, B. J. A. Cooke, J. Chem. Soc. Perkin Trans. 1 1973, 1026-1030;
30. b) P. Yates, N. Yoda, W. Brown, B. Mann, J. Am. Chem. Soc. 1958, 80, 202-205;
31. c) P. E. Eaton, C. Giordano, G. Schloemer, U. Vogel, J. Org. Chem. 1976, 41, 2238-2241.
32. a) A. Hosomi, H. Sakurai, J. Am. Chem. Soc. 1977, 99, 1673-1675;
33. b) H. Sakurai, A. Hosomi, J. Hayashi, Org. Synth. 1984, 62, 86-94.
34. a) H.-J. Knölker, J. Prakt. Chem. 1997, 339, 304-314;
35. b) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, Angew. Chem. 1993, 105, 1104-1106; Angew. Chem. Int. Ed. Engl. 1993, 32, 1081-1083;
36. b) H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, Angew. Chem. 1993, 105, 1104-1106; Angew. Chem. Int. Ed. Engl. 1993, 32, 1081-1083;
37. c) G. Hagen, H. Mayr, J. Am. Chem Soc. 1991, 113, 4954-4961.
38. [5]
39. F. G. West, P. V. Fisher, G. U. Gunawardena, S. Mitchell, Tetrahedron Lett. 1993, 34, 4583-4586.
40. R. Noyori, F. Shimizu, K. Fukuta, H. Takaya, Y. Hayakawa, J. Am. Chem. Soc. 1977, 99, 5196-5198.