Sakurai addition and ring annulation of allylsilanes with α,β- unsaturated esters. Experimental results and ab initio theoretical predictions examining allylsilane reactivity

Journal of Organic Chemistry

Volumn 65, Issue 12, 2000, Pages 3666-3678

  Organ, Michael G ^a   Dragan, Vladimir ^a   Miller, Michael ^a   Froese, Robert D J ^b   Goddard, John D ^b  

^a YORK UNIVERSITY   (Canada)

^b UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; PREDICTION; STRUCTURE ANALYSIS; THEORY;

EID: 0034674613     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991177i     Document Type: Article

References (91)

1. (a) Organ, M. G.; Winkle, D. J. Org. Chem. 1997, 62, 1881-1885.
2. (b) Organ, M. G.; Winkle, D. D.; Huffmann, J. J. Org. Chem. 1997, 62, 5254-5266.
3. Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1673-1675.
4. For general reviews on the uses of silicon in organic synthesis, see: (a) Fleming, I. Tildon Lecture. Some uses of silicon compounds in organic synthesis. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 356.
5. For general reviews on the uses of silicon in organic synthesis, see: (a) Fleming, I. Tildon Lecture. Some uses of silicon compounds in organic synthesis. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 356.
6. For general reviews on the uses of silicon in organic synthesis, see: (a) Fleming, I. Tildon Lecture. Some uses of silicon compounds in organic synthesis. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 356.
7. For general reviews on the uses of silicon in organic synthesis, see: (a) Fleming, I. Tildon Lecture. Some uses of silicon compounds in organic synthesis. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 356.
8. For general reviews on the uses of silicon in organic synthesis, see: (a) Fleming, I. Tildon Lecture. Some uses of silicon compounds in organic synthesis. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 356.
9. For general reviews on the uses of silicon in organic synthesis, see: (a) Fleming, I. Tildon Lecture. Some uses of silicon compounds in organic synthesis. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 356.
10. For general reviews on the uses of silicon in organic synthesis, see: (a) Fleming, I. Tildon Lecture. Some uses of silicon compounds in organic synthesis. Chem. Soc. Rev. 1981, 10, 83-111. (b) Parnes, Z. N.; Bolestova, G. I. Synthesis 1984, 991-1008. (c) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873. (d) Schinzer, D. Synthesis 1988, 263-273. (e) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 31, 57-575. (f) Chan, T. H.; Wang, D.; Pellon, P.; Lamothe, S.; Wie, Z. Y.; Li, L. H.; Chen, L. M. Enantioselective synthesis using silicon compounds. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 344-355. (g) Colvin, E. W.; Loreto, M. A.; Montieth, M.; Tommasini, I. Frontiers of Organosilicon Chemistry; The Royal Society of Chemistry: London, 1991; pp 356.
11. For approaches to four-membered rings using allylsilanes, see: (a) Hartman, G. D.; Traylor, T. G. Tetrahedron Lett. 1975, 16, 939-942. (b) Ochiai, M.; Arimoto, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1981, 460-461. (c) Paquette, L. A.; Valpey, R. S.; Annis, G. D. J. Org. Chem. 1984, 49, 1317-1319. (d) Fujiwara, T.; Suda, A.; Takeda, T. Chem. Lett. 1982, 1631-1634. (e) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (f) Akiyama, T.; Kirino, M. Chem. Lett. 1995, 723-724.
12. For approaches to four-membered rings using allylsilanes, see: (a) Hartman, G. D.; Traylor, T. G. Tetrahedron Lett. 1975, 16, 939- 942. (b) Ochiai, M.; Arimoto, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1981, 460-461. (c) Paquette, L. A.; Valpey, R. S.; Annis, G. D. J. Org. Chem. 1984, 49, 1317-1319. (d) Fujiwara, T.; Suda, A.; Takeda, T. Chem. Lett. 1982, 1631-1634. (e) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (f) Akiyama, T.; Kirino, M. Chem. Lett. 1995, 723-724.
13. For approaches to four-membered rings using allylsilanes, see: (a) Hartman, G. D.; Traylor, T. G. Tetrahedron Lett. 1975, 16, 939- 942. (b) Ochiai, M.; Arimoto, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1981, 460-461. (c) Paquette, L. A.; Valpey, R. S.; Annis, G. D. J. Org. Chem. 1984, 49, 1317-1319. (d) Fujiwara, T.; Suda, A.; Takeda, T. Chem. Lett. 1982, 1631-1634. (e) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (f) Akiyama, T.; Kirino, M. Chem. Lett. 1995, 723-724.
14. For approaches to four-membered rings using allylsilanes, see: (a) Hartman, G. D.; Traylor, T. G. Tetrahedron Lett. 1975, 16, 939- 942. (b) Ochiai, M.; Arimoto, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1981, 460-461. (c) Paquette, L. A.; Valpey, R. S.; Annis, G. D. J. Org. Chem. 1984, 49, 1317-1319. (d) Fujiwara, T.; Suda, A.; Takeda, T. Chem. Lett. 1982, 1631-1634. (e) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (f) Akiyama, T.; Kirino, M. Chem. Lett. 1995, 723-724.
15. For approaches to four-membered rings using allylsilanes, see: (a) Hartman, G. D.; Traylor, T. G. Tetrahedron Lett. 1975, 16, 939- 942. (b) Ochiai, M.; Arimoto, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1981, 460-461. (c) Paquette, L. A.; Valpey, R. S.; Annis, G. D. J. Org. Chem. 1984, 49, 1317-1319. (d) Fujiwara, T.; Suda, A.; Takeda, T. Chem. Lett. 1982, 1631-1634. (e) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (f) Akiyama, T.; Kirino, M. Chem. Lett. 1995, 723-724.
16. For approaches to four-membered rings using allylsilanes, see: (a) Hartman, G. D.; Traylor, T. G. Tetrahedron Lett. 1975, 16, 939- 942. (b) Ochiai, M.; Arimoto, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1981, 460-461. (c) Paquette, L. A.; Valpey, R. S.; Annis, G. D. J. Org. Chem. 1984, 49, 1317-1319. (d) Fujiwara, T.; Suda, A.; Takeda, T. Chem. Lett. 1982, 1631-1634. (e) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (f) Akiyama, T.; Kirino, M. Chem. Lett. 1995, 723-724.
17. For approaches to five-membered rings carbocycles using allylsilanes, see: (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097. (b) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (c) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845-3848. (d) Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765-4768. (e) Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958-1960. (f) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144-5146. (g) Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121-2122. (i) Akiyama, T.; Yamanaka, M. Tetrahedron Lett. 1998, 39, 7885-7888.
18. For approaches to five-membered rings carbocycles using allylsilanes, see: (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097. (b) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (c) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845-3848. (d) Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765-4768. (e) Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958-1960. (f) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144-5146. (g) Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121-2122. (i) Akiyama, T.; Yamanaka, M. Tetrahedron Lett. 1998, 39, 7885-7888.
19. For approaches to five-membered rings carbocycles using allylsilanes, see: (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097. (b) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (c) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845-3848. (d) Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765-4768. (e) Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958-1960. (f) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144-5146. (g) Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121-2122. (i) Akiyama, T.; Yamanaka, M. Tetrahedron Lett. 1998, 39, 7885-7888.
20. For approaches to five-membered rings carbocycles using allylsilanes, see: (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097. (b) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (c) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845-3848. (d) Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765-4768. (e) Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958-1960. (f) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144-5146. (g) Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121-2122. (i) Akiyama, T.; Yamanaka, M. Tetrahedron Lett. 1998, 39, 7885-7888.
21. For approaches to five-membered rings carbocycles using allylsilanes, see: (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097. (b) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (c) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845-3848. (d) Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765-4768. (e) Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958-1960. (f) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144-5146. (g) Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121-2122. (i) Akiyama, T.; Yamanaka, M. Tetrahedron Lett. 1998, 39, 7885-7888.
22. For approaches to five-membered rings carbocycles using allylsilanes, see: (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097. (b) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (c) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845-3848. (d) Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765-4768. (e) Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958-1960. (f) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144-5146. (g) Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121-2122. (i) Akiyama, T.; Yamanaka, M. Tetrahedron Lett. 1998, 39, 7885-7888.
23. For approaches to five-membered rings carbocycles using allylsilanes, see: (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097. (b) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (c) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845-3848. (d) Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765-4768. (e) Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958-1960. (f) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144-5146. (g) Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121-2122. (i) Akiyama, T.; Yamanaka, M. Tetrahedron Lett. 1998, 39, 7885-7888.
24. For approaches to five-membered rings carbocycles using allylsilanes, see: (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097. (b) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (c) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845-3848. (d) Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765-4768. (e) Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958-1960. (f) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144-5146. (g) Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121-2122. (i) Akiyama, T.; Yamanaka, M. Tetrahedron Lett. 1998, 39, 7885-7888.
25. For approaches to five-membered rings carbocycles using allylsilanes, see: (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097. (b) Hojo, M.; Tomita, K.; Hirohara, Y.; Hosomi, A. Tetrahedron Lett. 1993, 34, 8123-8126. (c) Danheiser, R. L.; Takahashi, T.; Bertók, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845-3848. (d) Knölker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765-4768. (e) Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958-1960. (f) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144-5146. (g) Takahashi, Y.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 1996, 37, 5943-5946. (h) Akiyama, T.; Hoshi, E.; Fujiyoshi, S. J. Chem. Soc., Perkin Trans. 1 1998, 2121-2122. (i) Akiyama, T.; Yamanaka, M. Tetrahedron Lett. 1998, 39, 7885-7888.
26. For approaches to substituted furans using allylsilanes, see: (a) Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868-9870. (b) Panek, J. S.; Beresis, R. J. Org. Chem. 1993, 58, 809-811. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1993, 58, 2345-2348. (d) Akiyama, T.; Yasusa, T.; Ishikawa, K.; Ozaki, S. Tetrahedron Lett. 1994, 35, 8401- 8404.
27. For approaches to substituted furans using allylsilanes, see: (a) Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868-9870. (b) Panek, J. S.; Beresis, R. J. Org. Chem. 1993, 58, 809-811. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1993, 58, 2345-2348. (d) Akiyama, T.; Yasusa, T.; Ishikawa, K.; Ozaki, S. Tetrahedron Lett. 1994, 35, 8401- 8404.
28. For approaches to substituted furans using allylsilanes, see: (a) Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868-9870. (b) Panek, J. S.; Beresis, R. J. Org. Chem. 1993, 58, 809-811. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1993, 58, 2345-2348. (d) Akiyama, T.; Yasusa, T.; Ishikawa, K.; Ozaki, S. Tetrahedron Lett. 1994, 35, 8401- 8404.
29. For approaches to substituted furans using allylsilanes, see: (a) Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868-9870. (b) Panek, J. S.; Beresis, R. J. Org. Chem. 1993, 58, 809-811. (c) Panek, J. S.; Jain, N. F. J. Org. Chem. 1993, 58, 2345-2348. (d) Akiyama, T.; Yasusa, T.; Ishikawa, K.; Ozaki, S. Tetrahedron Lett. 1994, 35, 8401-8404.
30. (a) Knölker, H.-J.; Jones, P. G.; Pannek, J.-B. Synlett 1990, 429-430.
31. (b) Knölker, H.-J.; Jones, P. G.; Pannek, J.-B.; Weinkauf, A. Synlett 1991, 147-150.
32. (c) Knölker, H.-J.; Foitzik, N.; Graf, R.; Pannek, J.-B. Tetrahedron 1993, 49, 9955-9972.
33. (d) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081-1083.
34. Murphy, W. S.; Neville, D. Tetrahedron Lett. 1997, 38, 7933-7936.
35. Allyltrimethylsilane has been successfully added to methyl propiolate, a much more reactive electrophile: Monti, H.; Audran, G.; Léandri, G.; Monti, J.-P. Tetrahedron Lett. 1994, 35, 3073-3076.
36. Knölker, H.-J.; Baum, G.; Graf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1612-1615.
37. For discussions regarding silyl-stabilized β-carbocations, see: (a) Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829-836. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p. 81 (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845. (f) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689. (g) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126. (h) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734-2738. (i) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841. (j) Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227-5233.
38. For discussions regarding silyl-stabilized β-carbocations, see: (a) Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829-836. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p. 81 (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845. (f) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689. (g) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126. (h) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734-2738. (i) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841. (j) Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227-5233.
39. For discussions regarding silyl-stabilized β-carbocations, see: (a) Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829-836. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p. 81 (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845. (f) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689. (g) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126. (h) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734-2738. (i) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841. (j) Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227-5233.
40. For discussions regarding silyl-stabilized β-carbocations, see: (a) Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829-836. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p. 81 (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845. (f) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689. (g) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126. (h) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734-2738. (i) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841. (j) Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227-5233.
41. For discussions regarding silyl-stabilized β-carbocations, see: (a) Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829-836. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p. 81 (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845. (f) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689. (g) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126. (h) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734-2738. (i) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841. (j) Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227-5233.
42. For discussions regarding silyl-stabilized β-carbocations, see: (a) Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829-836. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p. 81 (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845. (f) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689. (g) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126. (h) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734-2738. (i) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841. (j) Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227-5233.
43. For discussions regarding silyl-stabilized β-carbocations, see: (a) Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829-836. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p. 81 (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845. (f) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689. (g) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126. (h) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734-2738. (i) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841. (j) Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227-5233.
44. For discussions regarding silyl-stabilized β-carbocations, see: (a) Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829-836. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p. 81 (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845. (f) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689. (g) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126. (h) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734-2738. (i) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841. (j) Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227-5233.
45. For discussions regarding silyl-stabilized β-carbocations, see: (a) Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829-836. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p. 81 (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845. (f) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689. (g) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126. (h) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734-2738. (i) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841. (j) Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227-5233.
46. For discussions regarding silyl-stabilized β-carbocations, see: (a) Hanstein, W.; Berwin, H. J.; Traylor, T. G. J. Am. Chem. Soc. 1970, 92, 829-836. (b) Eaborn, C. J. Chem. Soc., Chem. Commun. 1972, 1255. (c) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: London, 1976; p. 81 (d) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496-1500. (e) Lambert, J. B.; Wang, G.-T.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838-7845. (f) Lambert, J. B. Tetrahedron 1990, 46, 2677-2689. (g) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120-8126. (h) Green, A. J.; Kuan, Y.-L.; White, J. M. J. Org. Chem. 1995, 60, 2734-2738. (i) Gabelica, V.; Kresge, A. J. J. Am. Chem. Soc. 1996, 118, 3838-3841. (j) Chan, V. Y.; Clark, C. I.; Giordano, J.; Green, A. J.; Karalis, A.; White, J. M. J. Org. Chem. 1996, 61, 5227-5233.
47. For examinations of the β-effect in relation to different groups on silicon, see: (a) Brook, M. A.; Hadi, M. A.; Neuy, A. J. Chem. Soc., Chem. Commun. 1989, 957-958. (b) Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609-3616. (c) Dallaire, C.; Brook, M. A. Organometallics 1990, 9, 2873-2874. (d) McGibbon, G. A.; Brook, M. A.; Terlouw, J. K. J. Chem. Soc., Chem. Commun. 1992, 360-362. (e) Dallaire, C.; Brook, M. A. Organometallics 1993, 12, 2332-2338. (f) Brook, M. A.; Henry, C. Tetrahedron 1996, 52, 861-868.
48. For examinations of the β-effect in relation to different groups on silicon, see: (a) Brook, M. A.; Hadi, M. A.; Neuy, A. J. Chem. Soc., Chem. Commun. 1989, 957-958. (b) Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609-3616. (c) Dallaire, C.; Brook, M. A. Organometallics 1990, 9, 2873-2874. (d) McGibbon, G. A.; Brook, M. A.; Terlouw, J. K. J. Chem. Soc., Chem. Commun. 1992, 360-362. (e) Dallaire, C.; Brook, M. A. Organometallics 1993, 12, 2332-2338. (f) Brook, M. A.; Henry, C. Tetrahedron 1996, 52, 861-868.
49. For examinations of the β-effect in relation to different groups on silicon, see: (a) Brook, M. A.; Hadi, M. A.; Neuy, A. J. Chem. Soc., Chem. Commun. 1989, 957-958. (b) Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609-3616. (c) Dallaire, C.; Brook, M. A. Organometallics 1990, 9, 2873-2874. (d) McGibbon, G. A.; Brook, M. A.; Terlouw, J. K. J. Chem. Soc., Chem. Commun. 1992, 360-362. (e) Dallaire, C.; Brook, M. A. Organometallics 1993, 12, 2332-2338. (f) Brook, M. A.; Henry, C. Tetrahedron 1996, 52, 861-868.
50. For examinations of the β-effect in relation to different groups on silicon, see: (a) Brook, M. A.; Hadi, M. A.; Neuy, A. J. Chem. Soc., Chem. Commun. 1989, 957-958. (b) Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609-3616. (c) Dallaire, C.; Brook, M. A. Organometallics 1990, 9, 2873-2874. (d) McGibbon, G. A.; Brook, M. A.; Terlouw, J. K. J. Chem. Soc., Chem. Commun. 1992, 360-362. (e) Dallaire, C.; Brook, M. A. Organometallics 1993, 12, 2332-2338. (f) Brook, M. A.; Henry, C. Tetrahedron 1996, 52, 861-868.
51. For examinations of the β-effect in relation to different groups on silicon, see: (a) Brook, M. A.; Hadi, M. A.; Neuy, A. J. Chem. Soc., Chem. Commun. 1989, 957-958. (b) Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609-3616. (c) Dallaire, C.; Brook, M. A. Organometallics 1990, 9, 2873-2874. (d) McGibbon, G. A.; Brook, M. A.; Terlouw, J. K. J. Chem. Soc., Chem. Commun. 1992, 360-362. (e) Dallaire, C.; Brook, M. A. Organometallics 1993, 12, 2332-2338. (f) Brook, M. A.; Henry, C. Tetrahedron 1996, 52, 861-868.
52. For examinations of the β-effect in relation to different groups on silicon, see: (a) Brook, M. A.; Hadi, M. A.; Neuy, A. J. Chem. Soc., Chem. Commun. 1989, 957-958. (b) Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609-3616. (c) Dallaire, C.; Brook, M. A. Organometallics 1990, 9, 2873-2874. (d) McGibbon, G. A.; Brook, M. A.; Terlouw, J. K. J. Chem. Soc., Chem. Commun. 1992, 360-362. (e) Dallaire, C.; Brook, M. A. Organometallics 1993, 12, 2332-2338. (f) Brook, M. A.; Henry, C. Tetrahedron 1996, 52, 861-868.
53. (a) Mayr, H.; Hagen, G. J. Chem. Soc., Chem. Commun. 1989, 91-92.
54. (b) Mayr, H.; Bartl, J.; Hagen, G. Angew. Chem., Int. Ed. Engl. 1982, 31, 1613-1615.
55. (c) Mayr, H.; Patz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957.
56. (d) Mayr, H.; Gorath, G. J. Am. Chem. Soc. 1995, 117, 7862-7868.
57. The issue of electronic vs steric activation of the olefin of allylsilanes where silicon is substituted by large alkyl groups has been investigated by a number of groups. For studies which try to compartmentalize these two effects, see: (a) Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954-4961. (b) Panek, J. S.; Prock, A.; Eriks, K.; Giering, W. P. Organometallics 1990, 9, 2175-2176.
58. The issue of electronic vs steric activation of the olefin of allylsilanes where silicon is substituted by large alkyl groups has been investigated by a number of groups. For studies which try to compartmentalize these two effects, see: (a) Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954-4961. (b) Panek, J. S.; Prock, A.; Eriks, K.; Giering, W. P. Organometallics 1990, 9, 2175-2176.
59. Compound 13 has been prepared previously by another route and the spectral characterization corresponded well; see: Nakahara, Y.; Fujita, A.; Ogawa, T. Agric. Biol. Chem. 1987, 51, 1009-1015.
60. This study; see the Theoretical Considerations section and also ref 10.
61. (a) Fleming, I.; Henning, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29-31.
62. (b) Fleming, I.; Sanderson, E. J. Tetrahedron Lett. 1987, 28, 4229-4232.
63. (c) Knölker, H.-J.; Wanzl, G. Synlett 1995, 378-382.
64. (d) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662.
65. (a) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1696-1698.
66. (b) Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983-990.
67. (c) Tamao, K.; Kumada, M. Tetrahedron Lett. 1984, 25, 321-324.
68. Just following the completion of the work for this manuscript, two reports were disclosed on the oxidation of diphenyl-tert-butylsilane and diisopropylphenylsilane; see ref 5i and the following: Knölker, H.-J.; Jones, P. G.; Wanzel, G. Synlett 1998, 613-616.
69. (a) Snider, B. B.; Rodini, D. J.; Conn, R. S. E.; Sealfon, S. J. Am. Chem. Soc. 1979, 101, 5285-5293.
70. (b) Snider, B. B.; Rodini, D. J. Tetrahedron Lett. 1980, 21, 1815-1818.
71. For reports dealing with acid-catalyzed protodesilylation, see: (a) Coughlin, D. J.; Salomon, R. G. J. Org. Chem. 1979, 44, 3784-3790. (b) Pennanen, S. I. Synth. Commun. 1980, 10, 373-379. (c) Hosomi, A.; Iguchi, H.; Sasaki, J.-I.; Sakurai, H. Tetrahedron Lett. 1982, 551-554. (d) Ireland, R. E.; Varney, M. D. J. Am. Chem. Soc. 1984, 106, 3668-3670. (e) Shibasaki, M.; Fukasawa, E.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (f) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1994, 117, 9616-9617.
72. For reports dealing with acid-catalyzed protodesilylation, see: (a) Coughlin, D. J.; Salomon, R. G. J. Org. Chem. 1979, 44, 3784- 3790. (b) Pennanen, S. I. Synth. Commun. 1980, 10, 373-379. (c) Hosomi, A.; Iguchi, H.; Sasaki, J.-I.; Sakurai, H. Tetrahedron Lett. 1982, 551-554. (d) Ireland, R. E.; Varney, M. D. J. Am. Chem. Soc. 1984, 106, 3668-3670. (e) Shibasaki, M.; Fukasawa, E.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (f) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1994, 117, 9616-9617.
73. For reports dealing with acid-catalyzed protodesilylation, see: (a) Coughlin, D. J.; Salomon, R. G. J. Org. Chem. 1979, 44, 3784- 3790. (b) Pennanen, S. I. Synth. Commun. 1980, 10, 373-379. (c) Hosomi, A.; Iguchi, H.; Sasaki, J.-I.; Sakurai, H. Tetrahedron Lett. 1982, 551-554. (d) Ireland, R. E.; Varney, M. D. J. Am. Chem. Soc. 1984, 106, 3668-3670. (e) Shibasaki, M.; Fukasawa, E.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (f) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1994, 117, 9616-9617.
74. For reports dealing with acid-catalyzed protodesilylation, see: (a) Coughlin, D. J.; Salomon, R. G. J. Org. Chem. 1979, 44, 3784- 3790. (b) Pennanen, S. I. Synth. Commun. 1980, 10, 373-379. (c) Hosomi, A.; Iguchi, H.; Sasaki, J.-I.; Sakurai, H. Tetrahedron Lett. 1982, 551-554. (d) Ireland, R. E.; Varney, M. D. J. Am. Chem. Soc. 1984, 106, 3668-3670. (e) Shibasaki, M.; Fukasawa, E.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (f) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1994, 117, 9616-9617.
75. For reports dealing with acid-catalyzed protodesilylation, see: (a) Coughlin, D. J.; Salomon, R. G. J. Org. Chem. 1979, 44, 3784- 3790. (b) Pennanen, S. I. Synth. Commun. 1980, 10, 373-379. (c) Hosomi, A.; Iguchi, H.; Sasaki, J.-I.; Sakurai, H. Tetrahedron Lett. 1982, 551-554. (d) Ireland, R. E.; Varney, M. D. J. Am. Chem. Soc. 1984, 106, 3668-3670. (e) Shibasaki, M.; Fukasawa, E.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (f) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1994, 117, 9616-9617.
76. For reports dealing with acid-catalyzed protodesilylation, see: (a) Coughlin, D. J.; Salomon, R. G. J. Org. Chem. 1979, 44, 3784- 3790. (b) Pennanen, S. I. Synth. Commun. 1980, 10, 373-379. (c) Hosomi, A.; Iguchi, H.; Sasaki, J.-I.; Sakurai, H. Tetrahedron Lett. 1982, 551-554. (d) Ireland, R. E.; Varney, M. D. J. Am. Chem. Soc. 1984, 106, 3668-3670. (e) Shibasaki, M.; Fukasawa, E.; Ikegami, S. Tetrahedron Lett. 1983, 24, 3497-3500. (f) Corey, E. J.; Letavic, M. A. J. Am. Chem. Soc. 1994, 117, 9616-9617.
77. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian92; Gaussian Inc.: Pittsburgh, PA, 1992.
78. (a) Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939-947.
79. (b) Gordon, M. S.; Binkley, J. S.; Pople, J. A.; Pietro, W. J.; Hehre, W. J. J. Am. Chem. Soc. 1982, 104, 2797-2803.
80. (c) Pietro, W. J.; Francl, M. M.; Hehre, W. J.; Defrees, D. J.; Pople, J. A.; Binkley, J. S. J. Am. Chem. Soc. 1982, 104, 5039-5048.
81. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
82. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
83. (c) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
84. (a) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728.
85. (b) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
86. (c) Hariharan, P. C.; Pople, J. A. Mol. Phys. 1974, 27, 209-214.
87. (d) Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163-168.
88. (e) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
89. (a) Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503-506.
90. (b) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 275-280.
91. (c) Frisch, M. J.; Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 166, 281-289.