Highly Stereoselective Intramolecular Addition of a Hydroxyl Group to Vinylsilanes via 1,2-Silyl Migration

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8292-8293

  Miura, Katsukiyo ^a   Hondo, Takeshi ^a   Saito, Hiroshi ^a   Ito, Hajime ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000897326     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971847p     Document Type: Article

References (34)

1. Studies on Organosilicon Chemistry. 137.
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3. (b) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991; Vol. 1, p 579.
4. [3 + 2] cycloaddition of allylsilanes and the related compounds via the 1,2-silyl migration. See: (a) Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1996, 61, 3230. (b) Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496. (c) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941. (d) Knölker, H.-J.; Graf, R. Synlett 1994, 131, (e) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (g) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371. (h) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (i) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845 and references cited in these references. For a review of allylsilanes in organic synthesis, see: (j) Hosomi, A. Acc. Chem. Res. 1988, 27, 200.
5. [3 + 2] cycloaddition of allylsilanes and the related compounds via the 1,2-silyl migration. See: (a) Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1996, 61, 3230. (b) Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496. (c) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941. (d) Knölker, H.-J.; Graf, R. Synlett 1994, 131, (e) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (g) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371. (h) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (i) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845 and references cited in these references. For a review of allylsilanes in organic synthesis, see: (j) Hosomi, A. Acc. Chem. Res. 1988, 27, 200.
6. [3 + 2] cycloaddition of allylsilanes and the related compounds via the 1,2-silyl migration. See: (a) Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1996, 61, 3230. (b) Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496. (c) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941. (d) Knölker, H.-J.; Graf, R. Synlett 1994, 131, (e) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (g) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371. (h) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (i) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845 and references cited in these references. For a review of allylsilanes in organic synthesis, see: (j) Hosomi, A. Acc. Chem. Res. 1988, 27, 200.
7. [3 + 2] cycloaddition of allylsilanes and the related compounds via the 1,2-silyl migration. See: (a) Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1996, 61, 3230. (b) Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496. (c) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941. (d) Knölker, H.-J.; Graf, R. Synlett 1994, 131, (e) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (g) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371. (h) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (i) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845 and references cited in these references. For a review of allylsilanes in organic synthesis, see: (j) Hosomi, A. Acc. Chem. Res. 1988, 27, 200.
8. [3 + 2] cycloaddition of allylsilanes and the related compounds via the 1,2-silyl migration. See: (a) Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1996, 61, 3230. (b) Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496. (c) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941. (d) Knölker, H.-J.; Graf, R. Synlett 1994, 131, (e) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (g) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371. (h) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (i) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845 and references cited in these references. For a review of allylsilanes in organic synthesis, see: (j) Hosomi, A. Acc. Chem. Res. 1988, 27, 200.
9. [3 + 2] cycloaddition of allylsilanes and the related compounds via the 1,2-silyl migration. See: (a) Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1996, 61, 3230. (b) Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496. (c) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941. (d) Knölker, H.-J.; Graf, R. Synlett 1994, 131, (e) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (g) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371. (h) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (i) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845 and references cited in these references. For a review of allylsilanes in organic synthesis, see: (j) Hosomi, A. Acc. Chem. Res. 1988, 27, 200.
10. [3 + 2] cycloaddition of allylsilanes and the related compounds via the 1,2-silyl migration. See: (a) Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1996, 61, 3230. (b) Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496. (c) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941. (d) Knölker, H.-J.; Graf, R. Synlett 1994, 131, (e) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (g) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371. (h) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (i) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845 and references cited in these references. For a review of allylsilanes in organic synthesis, see: (j) Hosomi, A. Acc. Chem. Res. 1988, 27, 200.
11. [3 + 2] cycloaddition of allylsilanes and the related compounds via the 1,2-silyl migration. See: (a) Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1996, 61, 3230. (b) Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496. (c) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941. (d) Knölker, H.-J.; Graf, R. Synlett 1994, 131, (e) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (g) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371. (h) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (i) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845 and references cited in these references. For a review of allylsilanes in organic synthesis, see: (j) Hosomi, A. Acc. Chem. Res. 1988, 27, 200.
12. [3 + 2] cycloaddition of allylsilanes and the related compounds via the 1,2-silyl migration. See: (a) Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1996, 61, 3230. (b) Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496. (c) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941. (d) Knölker, H.-J.; Graf, R. Synlett 1994, 131, (e) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (g) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371. (h) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (i) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845 and references cited in these references. For a review of allylsilanes in organic synthesis, see: (j) Hosomi, A. Acc. Chem. Res. 1988, 27, 200.
13. [3 + 2] cycloaddition of allylsilanes and the related compounds via the 1,2-silyl migration. See: (a) Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1996, 61, 3230. (b) Schinzer, D.; Panke, G. J. Org. Chem. 1996, 61, 4496. (c) Suginome, M.; Matsunaga, S.; Ito, Y. Synlett 1995, 941. (d) Knölker, H.-J.; Graf, R. Synlett 1994, 131, (e) Akiyama, T.; Ishikawa, K.; Ozaki, S. Chem. Lett. 1994, 627. (f) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674. (g) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371. (h) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (i) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845 and references cited in these references. For a review of allylsilanes in organic synthesis, see: (j) Hosomi, A. Acc. Chem. Res. 1988, 27, 200.
14. For other reactions via the 1,2-silyl migration, see: (a) Tanino, K.; Yoshitani, N.; Moriyama, F.; Kuwajima, I. J. Org. Chem. 1997, 62, 4206. (b) Yamazaki, S.; Tanaka, M.; Yamabe, S. J. Org. Chem. 1996, 61, 4046 and references therein, (c) Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1994, 35, 6461. (d) Kang, K.-T.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 4953. (e) Hudrlik, P. F.; Hudrlik, A. M.; Nagendrappa, G.; Yimenu, T.; Zellers, E. T.; Chin, E. J. Am. Chem. Soc. 1980, 102, 6896; correction: ibid. 1982, 104, 1157.
15. For other reactions via the 1,2-silyl migration, see: (a) Tanino, K.; Yoshitani, N.; Moriyama, F.; Kuwajima, I. J. Org. Chem. 1997, 62, 4206. (b) Yamazaki, S.; Tanaka, M.; Yamabe, S. J. Org. Chem. 1996, 61, 4046 and references therein, (c) Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1994, 35, 6461. (d) Kang, K.-T.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 4953. (e) Hudrlik, P. F.; Hudrlik, A. M.; Nagendrappa, G.; Yimenu, T.; Zellers, E. T.; Chin, E. J. Am. Chem. Soc. 1980, 102, 6896; correction: ibid. 1982, 104, 1157.
16. For other reactions via the 1,2-silyl migration, see: (a) Tanino, K.; Yoshitani, N.; Moriyama, F.; Kuwajima, I. J. Org. Chem. 1997, 62, 4206. (b) Yamazaki, S.; Tanaka, M.; Yamabe, S. J. Org. Chem. 1996, 61, 4046 and references therein, (c) Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1994, 35, 6461. (d) Kang, K.-T.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 4953. (e) Hudrlik, P. F.; Hudrlik, A. M.; Nagendrappa, G.; Yimenu, T.; Zellers, E. T.; Chin, E. J. Am. Chem. Soc. 1980, 102, 6896; correction: ibid. 1982, 104, 1157.
17. For other reactions via the 1,2-silyl migration, see: (a) Tanino, K.; Yoshitani, N.; Moriyama, F.; Kuwajima, I. J. Org. Chem. 1997, 62, 4206. (b) Yamazaki, S.; Tanaka, M.; Yamabe, S. J. Org. Chem. 1996, 61, 4046 and references therein, (c) Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1994, 35, 6461. (d) Kang, K.-T.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 4953. (e) Hudrlik, P. F.; Hudrlik, A. M.; Nagendrappa, G.; Yimenu, T.; Zellers, E. T.; Chin, E. J. Am. Chem. Soc. 1980, 102, 6896; correction: ibid. 1982, 104, 1157.
18. For other reactions via the 1,2-silyl migration, see: (a) Tanino, K.; Yoshitani, N.; Moriyama, F.; Kuwajima, I. J. Org. Chem. 1997, 62, 4206. (b) Yamazaki, S.; Tanaka, M.; Yamabe, S. J. Org. Chem. 1996, 61, 4046 and references therein, (c) Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1994, 35, 6461. (d) Kang, K.-T.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 4953. (e) Hudrlik, P. F.; Hudrlik, A. M.; Nagendrappa, G.; Yimenu, T.; Zellers, E. T.; Chin, E. J. Am. Chem. Soc. 1980, 102, 6896; correction: ibid. 1982, 104, 1157.
19. For other reactions via the 1,2-silyl migration, see: (a) Tanino, K.; Yoshitani, N.; Moriyama, F.; Kuwajima, I. J. Org. Chem. 1997, 62, 4206. (b) Yamazaki, S.; Tanaka, M.; Yamabe, S. J. Org. Chem. 1996, 61, 4046 and references therein, (c) Angle, S. R.; Boyce, J. P. Tetrahedron Lett. 1994, 35, 6461. (d) Kang, K.-T.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 4953. (e) Hudrlik, P. F.; Hudrlik, A. M.; Nagendrappa, G.; Yimenu, T.; Zellers, E. T.; Chin, E. J. Am. Chem. Soc. 1980, 102, 6896; correction: ibid. 1982, 104, 1157.
20. (a) Miura, K; Okajima, S.; Hondo, T.; Hosomi, A. Tetrahedron Lett. 1995, 36, 1483.
21. (b) Miura, K; Hondo, T.; Okajima, S.; Hosomi, A. Tetrahedron Lett. 1996, 37, 487.
22. 1H NMR analysis.
23. The high reactivity of 1d is probably due to electron-donating ability of the tert-butyl group, which accelerates proton addition to the α-carbon (step 2 in Scheme 1). The phenyl group of 1a or 1c would rather act as an electron-withdrawing substituent and reduce the reactivity of the double bond toward protonation. Mayr, H.; Patz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 938.
24. We have shown that the cyclization of 1 (R = H) to 3 proceeds in a syn addition mode of the hydroxyl group and proposed the oxonium ion intermediate from the stereochemical outcome. See ref 5.
25. For the activating and directive effects of silicon, see: Bassindale, A. R.; Taylor, P. G. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Ed.; Wiley: Chichester, 1989; Part 2, p 893.
26. (a) Schweig, A.; Weidner, U.; Manuel, G. J. Organomet. Chem. 1974, 67, C4.
27. (b) Brown, R. S.; Eaton, D. F.; Hosomi, A.; Traylor, T. G.; Wright, J. M. J. Organomet. Chem. 1974, 66, 249.
28. There is a longstanding dispute on the structure of β-silyl carbenium ions, which can take a hyperconjugatively stabilized open form or a bridged form. Although the open forms 7 and 8 are employed in Scheme 1, when R is an alkyl group, they can be displaced to one bridged intermediate without any problems. Lambert, J. B.; Zhao, Y. J. Am. Chem. Soc. 1996, 118, 7867.
29. Although the fast cyclization of 8 compared with 7, that is, kinetic control, can be responsible for the exclusive formation of trans-2d, we do not have any reliable evidence that trans-2d is a kinetically favored product.
30. See the Supporting Information.
31. Recently, Kuwajima et al. have reported novel ring expansion reactions with the 1,2-silyl migration. See ref 4a.
32. The MM2 calculation of the steric energy using the CAChe system (Sony/Tektronix Co. Ltd.) indicates that trans-2d is more stable by 3.5 kcal/mol than (2R*,1′S*)-3d in their optimized structures.
33. (a) Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C 37.
34. (b) Murakami, M.; Suginome, M.; Fujimoto, K.; Nakamura, H.; Andersson, P. G.; Ito, Y. J. Am. Chem. Soc. 1993, 115, 6487.