Cycloadditions of allylsilanes. Part 10: Stereoselective contruction of ring systems by cycloaddition reactions of allyltriisopropylsilane

Journal fur Praktische Chemie - Chemiker - Zeitung

Volumn 339, Issue 4, 1997, Pages 304-314

  Knolker H J ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750166300     PISSN: 09411216     EISSN: None     Source Type: Journal    
DOI: 10.1002/prac.19973390158     Document Type: Review

References (78)

1. Part 9: H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, P. G. Jones, G. Wanzl, Chem. Eur. J. 3 (1997) 538
2. H. Sakurai, Pure Appl. Chem. 54 (1982) 1;
3. A. Hosomi, Acc. Chem. Res. 21 (1988) 200;
4. I. Fleming, J. Dunoguès, R. Smithers, Org. React. 37 (1989) 57;
5. I. Fleming in "Comprehensive Organic Synthesis", ed. C. H. Heathcock, Pergamon, Oxford 1991, vol. 2, p. 563;
6. C. E. Masse, J. S. Panek, Chem. Rev. 95 (1995) 1293;
7. E. Langkopf, D. Schinzer, Chem. Rev. 95 (1995) 1375
8. D. Schinzer, J. Prakt. Chem. 336 (1994) 375
9. A. Hosomi, H. Sakurai, J. Am. Chem. Soc. 99 (1977) 1673;
10. T. A. Blumenkopf, C. H. Heathcock, J. Am. Chem. Soc. 105 (1983) 2354;
11. D. Schinzer, Synthesis 1988, 263;
12. G. Majetich in "Organic Synthesis, Theory and Applications", ed. T. Hudlicky, JAI Press, Greenwich (CT) 1989, vol. 1, p. 173
13. H.-J. Knölker, P. G. Jones, J.-B. Pannek, Synlett 1990, 429
14. H.-J. Knölker, P. G. Jones, J.-B. Pannek, A. Weinkauf, Synlett 1991, 147
15. H.-J. Knölker in "Organic Synthesis via Organometallics", eds. K. H. Dötz R. W. Hoffmann, Vieweg, Braunschweig 1991, p. 119;
16. H.-J. Knölker, Synlett 1992, 371
17. H.-J. Knölker, N. Foitzik, R. Graf, J.-B. Pannek, P. G. Jones, Tetrahedron 49 (1993) 9955
18. H.-J. Knölker, N. Foitzik, H. Goesmann, R. Graf, Angew. Chem. 105 (1993) 1104;
19. Angew. Chem., Int. Ed. Engl. 32 (1993) 1081;
20. this work was presented first at the 8th ORCHEM meeting in Bad Nauheim, September 24-26, 1992
21. G. Hagen, H. Mayr, J. Am. Chem. Soc. 113 (1991) 4954
22. Aldrich Chemical Co.: Allyltriisopropylsilane (art. 33,806-0)
23. R. L. Danheiser, B. R. Dixon, R. W. Gleason, J. Org. Chem. 57 (1992) 6094
24. H.-J. Knölker, R. Graf, Tetrahedron Lett. 34 (1993) 4765
25. R. L. Danheiser, T. Takahashi, B. Bertók, B. R. Dixon, Tetrahedron Lett. 34 (1993) 3845
26. J. S. Panek, N. F. Jain, J. Org. Chem. 58 (1993) 2345
27. For reviews, see: T.-L. Ho, Tandem Organic Reactions, Wiley, Chichester, 1992;
28. L. F. Tietze, U. Beifuss, Angew. Chem. 105 (1993) 137;
29. Angew. Chem., Int. Ed. Engl. 32 (1993) 131
30. R. Mitschka, J. Oehldrich, K. Takahashi, J. M. Cook, U. Weiss, J. V. Silverton, Tetrahedron 37 (1981) 4521;
31. S. H. Bertz, J. M. Cook, A. Gawish, U. Weiss, Org. Synth. 64 (1986) 27
32. H.-J. Knölker, R. Graf, Synlett 1994, 131
33. H.-J. Knölker, E. Baum, R. Graf, unpublished results
34. H.-J. Knölker, P. G. Jones, R. Graf, Synlett 1996, 1155
35. L. Fitjer, H. Monzó-Oltra, M. Noltemeyer, Angew. Chem. 103 (1991) 1534;
36. Angew. Chem., Int. Ed. Engl. 30 (1991) 1492;
37. B. M. Trost, Y. Shi, J. Am. Chem. Soc. 115 (1993) 9421;
38. L. Fitjer, M. Majewski, H. Monzó-Oltra, Tetrahedron 51 (1995) 8835
39. T. Akiyama, K. Ishikawa, S. Ozaki, Chem. Lett. 1994, 627
40. T. Akiyama, T. Yasusa, K. Ishikawa, S. Ozaki, Tetrahedron Lett. 35 (1994) 8401
41. J. S. Panek, M. Yang, J. Am. Chem. Soc. 113 (1991) 9868;
42. J. S. Panek, R. Beresis, J. Org. Chem. 58 (1993) 809
43. D. Schinzer, G. Panke, J. Org. Chem. 61 (1996) 4496
44. S. R. Angle, J. P. Boyce, Tetrahedron Lett. 35 (1994) 6461
45. R. Pardo, J.-P. Zhara, M. Santelli, Tetrahedron Lett. 1979, 4557;
46. A. Hosomi, H. Kobayashi, H. Sakurai, Tetrahedron Lett. 21 (1980) 955;
47. S. Danishefsky, M. Kahn, Tetrahedron Lett. 22 (1981) 485;
48. H. O. House, P. C. Gaa, D. VanDerveer, J. Org. Chem. 48 (1983) 1661;
49. G. Majetich, J. Defauw, C. Ringold, J. Org. Chem. 53 (1988) 50;
50. K. Nickisch, H. Laurent, Tetrahedron Lett. 29 (1988) 1533;
51. G. Majetich, K. Hull, D. Lowery, C. Ringold, J. Defauw in "Selectivities in Lewis Promoted Reactions", ed. D. Schinzer, Kluwer, Dordrecht 1989, p. 169;
52. G. Majetich, J.-S. Song, C. Ringold, G. A. Nemeth, Tetrahedron Lett. 31 (1990) 2239
53. G. Majetich, J.-S. Song, C. Ringold, G. A. Nemeth, M. G. Newton, J. Org. Chem. 56 (1991) 3973;
54. G. Majetich in "Strategies and Tactics in Organic Synthesis", ed. T. Lindberg, Academic Press, San Diego 1991, vol. 3, p. 295
55. G. D. Hartmann, T. G. Traylor, Tetrahedron Lett. 1975, 939;
56. M. Ochiai, M. Arimoto, E. Fujita, J. Chem. Soc. Chem. Commun. 1981, 460;
57. S. Ohashi, W. E. Ruch, G. B. Butler, J. Org. Chem. 46 (1981) 614;
58. S. Imazu, N. Shimizu, Y. Tsuno, Chem. Lett. 1990, 1845;
59. R. Huisgen, R. Brückner, Tetrahedron Lett. 31 (1990) 2553
60. H.-J. Knölker, G. Baum, R. Graf, Angew. Chem. 106 (1994) 1705;
61. Angew. Chem., Int. Ed. Engl. 33 (1994) 1612
62. H. Monti, G. Audran, J.-P. Monti, G. Léandri, Synlett 1994, 403;
63. G. P. Brengel, C. Rithner, A. I. Meyers, J. Org. Chem. 59 (1994) 5144
64. T. Akiyama, M. Kirino, Chem. Lett. 1995, 723
65. T. Akiyama, M. Yamanaka, Synlett 1996, 1095
66. T. Uyehara, M. Yuuki, H. Masaki, M. Matsumoto, M. Ueno, T. Sato, Chem. Lett. 1995, 789
67. J. S. Panek, N. F. Jain, J. Org. Chem. 59 (1994) 2674
68. J. R. Hwu, C. N. Chen, S.-S. Shiao, J. Org. Chem. 60 (1995) 856
69. I. Fleming, R. Henning, H. Plaut, J. Chem. Soc. Chem. Commun. 1984, 29;
70. I. Fleming, P. E. J. Sanderson, Tetrahedron Lett. 36 (1987) 4229;
71. I. Fleming, R. Henning, D. C. Parker, H. E. Plaut, P. E. J. Sanderson, J. Chem. Soc., Perkins Trans. 1 1995, 317
72. K. Tamao, T. Kakui, M. Akita, T. Iwahara, R. Kanatani, J. Oshida, M. Kumada, Tetrahedron 39 (1983) 983;
73. K. Tamao, N. Ishida, T. Tanaka, K. Kumada, Organometallics 2 (1983) 1694;
74. K. Tamao, N. Ishida, J. Organomet. Chem. 269 (1984) C37
75. For recent reviews, see: I. Fleming, Chemtracts-Organic Chemistry 9 (1996) 1;
76. G. R. Jones, Y. Landais, Tetrahedron 52 (1996) 7599
77. H.-J. Knölker, G. Wanzl, Synlett 1995, 378;
78. for a more recent example, see: G. P. Brengel, A. I. Meyers, J. Org. Chem. 61 (1996) 3230