tert-Butyldimethylsilyldihalomethyllithium as a dihalomethylene dianion synthon. 1,3-Rearrangement and 1,4-rearrangement of silyl group from carbon to oxide

Tetrahedron

Volumn 52, Issue 2, 1996, Pages 503-514

  Shinokubo, Hiroshi ^a   Miura, Katsukiyo ^a   Oshima, Koichiro ^a   Utimoto, Kiitiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOSILICON DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030030939     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00903-5     Document Type: Article

References (45)

1. Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886; Brook, A. G.; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981; Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224; Brook, A. G. Acc. Chem. Res. 1974, 7, 77; Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 2, pp 149-227.
2. Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886; Brook, A. G.; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981; Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224; Brook, A. G. Acc. Chem. Res. 1974, 7, 77; Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 2, pp 149-227.
3. Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886; Brook, A. G.; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981; Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224; Brook, A. G. Acc. Chem. Res. 1974, 7, 77; Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 2, pp 149-227.
4. Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886; Brook, A. G.; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981; Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224; Brook, A. G. Acc. Chem. Res. 1974, 7, 77; Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 2, pp 149-227.
5. Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886; Brook, A. G.; Warner, C. M.; McGriskin, M. E. J. Am. Chem. Soc. 1959, 81, 981; Brook, A. G.; Pascoe, J. D. J. Am. Chem. Soc. 1971, 93, 6224; Brook, A. G. Acc. Chem. Res. 1974, 7, 77; Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 2, pp 149-227.
6. Linderman, R. J.; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 2392; Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 835; Danheiser, R. L.; Fink, D. M.; Okano, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393; Kuwajima, I.; Kato, M.; Mon, A. Tetrahedron Lett. 1980, 21, 2745; Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423.
7. Linderman, R. J.; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 2392; Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 835; Danheiser, R. L.; Fink, D. M.; Okano, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393; Kuwajima, I.; Kato, M.; Mon, A. Tetrahedron Lett. 1980, 21, 2745; Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423.
8. Linderman, R. J.; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 2392; Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 835; Danheiser, R. L.; Fink, D. M.; Okano, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393; Kuwajima, I.; Kato, M.; Mon, A. Tetrahedron Lett. 1980, 21, 2745; Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423.
9. Linderman, R. J.; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 2392; Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 835; Danheiser, R. L.; Fink, D. M.; Okano, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393; Kuwajima, I.; Kato, M.; Mon, A. Tetrahedron Lett. 1980, 21, 2745; Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423.
10. Linderman, R. J.; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 2392; Koreeda, M.; Koo, S. Tetrahedron Lett. 1990, 31, 835; Danheiser, R. L.; Fink, D. M.; Okano, K.; Tsai, Y.-M.; Szczepanski, S. W. J. Org. Chem. 1985, 50, 5393; Kuwajima, I.; Kato, M.; Mon, A. Tetrahedron Lett. 1980, 21, 2745; Reich, H. J.; Olson, R. E.; Clark, M. C. J. Am. Chem. Soc. 1980, 102, 1423.
11. 2-carbon to oxide has been reported. Ito, Y.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1987, 109, 7888.
12. 2-carbon to oxide has been reported. Ito, Y.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1987, 109, 7888.
13. 2-carbon to oxide has been reported. Ito, Y.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1987, 109, 7888.
14. 2-carbon to oxide has been reported. Ito, Y.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1987, 109, 7888.
15. 2-carbon to oxide has been reported. Ito, Y.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1987, 109, 7888.
16. 2-carbon to oxide has been reported. Ito, Y.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1987, 109, 7888.
17. 2-carbon to oxide has been reported. Ito, Y.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1987, 109, 7888.
18. Tandem transformations initiated by the migration of a silyl group have been reviewed. Jankowski, P.; Raubo, P.; Wicha, J. Synlett 1994, 985.
19. A part of this work was published in a communication. Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 54, 1951.
20. 2 1b was generated in 85% yield. Bacquet, C.; Masure, D.; Normant, J. F. Bull. Soc. Chim. Fr. 1975, 1797.
21. Burford, C.; Cooke, F.; Ehlinger, E.; Magnus, P. D. J. Am. Chem. Soc. 1977, 99, 4536.
22. Seebach, D.; Grobel, B.-T.; Beck, A. K.; Braun, M.; Geiss, K.-H. Angew. Chem. Int. Ed. Engl. 1972, 11, 443; Carey, F. A.; Court, A. S.; J. Org. Chem. 1972, 37, 1926; Jones, P. F.; Lappert, M. F.; Szary, A. C. J. Chem. Soc., Perkin Trans. 1, 1973, 2272; Seebach, D.; Kolb, M.; Grobel, B.-T. Chem. Ber. 1973, 106, 2277.
23. Seebach, D.; Grobel, B.-T.; Beck, A. K.; Braun, M.; Geiss, K.-H. Angew. Chem. Int. Ed. Engl. 1972, 11, 443; Carey, F. A.; Court, A. S.; J. Org. Chem. 1972, 37, 1926; Jones, P. F.; Lappert, M. F.; Szary, A. C. J. Chem. Soc., Perkin Trans. 1, 1973, 2272; Seebach, D.; Kolb, M.; Grobel, B.-T. Chem. Ber. 1973, 106, 2277.
24. Seebach, D.; Grobel, B.-T.; Beck, A. K.; Braun, M.; Geiss, K.-H. Angew. Chem. Int. Ed. Engl. 1972, 11, 443; Carey, F. A.; Court, A. S.; J. Org. Chem. 1972, 37, 1926; Jones, P. F.; Lappert, M. F.; Szary, A. C. J. Chem. Soc., Perkin Trans. 1, 1973, 2272; Seebach, D.; Kolb, M.; Grobel, B.-T. Chem. Ber. 1973, 106, 2277.
25. Seebach, D.; Grobel, B.-T.; Beck, A. K.; Braun, M.; Geiss, K.-H. Angew. Chem. Int. Ed. Engl. 1972, 11, 443; Carey, F. A.; Court, A. S.; J. Org. Chem. 1972, 37, 1926; Jones, P. F.; Lappert, M. F.; Szary, A. C. J. Chem. Soc., Perkin Trans. 1, 1973, 2272; Seebach, D.; Kolb, M.; Grobel, B.-T. Chem. Ber. 1973, 106, 2277.
26. The yields are based on benzaldehyde employed.
27. 2 and aldehyde has been reported. Hosomi, A.; Inaba, M.; Sakurai, H. Tetrahedron Lett., 1983, 24, 4727.
28. 2 and aldehyde has been reported. Hosomi, A.; Inaba, M.; Sakurai, H. Tetrahedron Lett., 1983, 24, 4727.
29. 2 and aldehyde has been reported. Hosomi, A.; Inaba, M.; Sakurai, H. Tetrahedron Lett., 1983, 24, 4727.
30. Tetrahydrofuran was less effective than DME-THF for 1,3-migration of silicon (3 → 4).
31. 2CH(OH)Ph in 88% yield.
32. Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143.
33. Fujita and Hiyama have reported that bis(trimethylsilyl)dichloromethane reacted with 2 mol of benzaldehyde in the presence of TASF to give a 1:2 adduct. Fujita, M.; Hiyama, T. J. Am. Chem. Soc. 1985, 107, 4085.
34. tert-Butyldimethylsilyldibromomethyllithium (2a) was stable at -40°C but decomposed at -20°C in ether or THF.
35. 1,4-Migration of silicon from carbon to oxide has been reported. Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 43, 1947; Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc. Perkin Trans. 1, 1979, 26; Matsuda, I.; Murata, S.; Izumi, Y. Bull. Chem. Soc. Jpn., 1979, 52, 2389; Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731; Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511; Fischer, M.-R.; Kirschning, A.; Michel, T.; Schaumann, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 217. 1,4-Migration of silicon from oxygen to carbon has been reported. Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021; Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270; Winter, E.; Brückner, R. Synlett 1994, 1049.
36. 1,4-Migration of silicon from carbon to oxide has been reported. Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 43, 1947; Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc. Perkin Trans. 1, 1979, 26; Matsuda, I.; Murata, S.; Izumi, Y. Bull. Chem. Soc. Jpn., 1979, 52, 2389; Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731; Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511; Fischer, M.-R.; Kirschning, A.; Michel, T.; Schaumann, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 217. 1,4-Migration of silicon from oxygen to carbon has been reported. Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021; Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270; Winter, E.; Brückner, R. Synlett 1994, 1049.
37. 1,4-Migration of silicon from carbon to oxide has been reported. Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 43, 1947; Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc. Perkin Trans. 1, 1979, 26; Matsuda, I.; Murata, S.; Izumi, Y. Bull. Chem. Soc. Jpn., 1979, 52, 2389; Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731; Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511; Fischer, M.-R.; Kirschning, A.; Michel, T.; Schaumann, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 217. 1,4-Migration of silicon from oxygen to carbon has been reported. Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021; Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270; Winter, E.; Brückner, R. Synlett 1994, 1049.
38. 1,4-Migration of silicon from carbon to oxide has been reported. Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 43, 1947; Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc. Perkin Trans. 1, 1979, 26; Matsuda, I.; Murata, S.; Izumi, Y. Bull. Chem. Soc. Jpn., 1979, 52, 2389; Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731; Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511; Fischer, M.-R.; Kirschning, A.; Michel, T.; Schaumann, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 217. 1,4-Migration of silicon from oxygen to carbon has been reported. Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021; Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270; Winter, E.; Brückner, R. Synlett 1994, 1049.
39. 1,4-Migration of silicon from carbon to oxide has been reported. Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 43, 1947; Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc. Perkin Trans. 1, 1979, 26; Matsuda, I.; Murata, S.; Izumi, Y. Bull. Chem. Soc. Jpn., 1979, 52, 2389; Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731; Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511; Fischer, M.-R.; Kirschning, A.; Michel, T.; Schaumann, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 217. 1,4-Migration of silicon from oxygen to carbon has been reported. Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021; Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270; Winter, E.; Brückner, R. Synlett 1994, 1049.
40. 1,4-Migration of silicon from carbon to oxide has been reported. Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 43, 1947; Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc. Perkin Trans. 1, 1979, 26; Matsuda, I.; Murata, S.; Izumi, Y. Bull. Chem. Soc. Jpn., 1979, 52, 2389; Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731; Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511; Fischer, M.-R.; Kirschning, A.; Michel, T.; Schaumann, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 217. 1,4-Migration of silicon from oxygen to carbon has been reported. Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021; Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270; Winter, E.; Brückner, R. Synlett 1994, 1049.
41. 1,4-Migration of silicon from carbon to oxide has been reported. Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 43, 1947; Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc. Perkin Trans. 1, 1979, 26; Matsuda, I.; Murata, S.; Izumi, Y. Bull. Chem. Soc. Jpn., 1979, 52, 2389; Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731; Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511; Fischer, M.-R.; Kirschning, A.; Michel, T.; Schaumann, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 217. 1,4-Migration of silicon from oxygen to carbon has been reported. Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021; Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270; Winter, E.; Brückner, R. Synlett 1994, 1049.
42. 1,4-Migration of silicon from carbon to oxide has been reported. Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 43, 1947; Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc. Perkin Trans. 1, 1979, 26; Matsuda, I.; Murata, S.; Izumi, Y. Bull. Chem. Soc. Jpn., 1979, 52, 2389; Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731; Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511; Fischer, M.-R.; Kirschning, A.; Michel, T.; Schaumann, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 217. 1,4-Migration of silicon from oxygen to carbon has been reported. Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021; Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270; Winter, E.; Brückner, R. Synlett 1994, 1049.
43. 1,4-Migration of silicon from carbon to oxide has been reported. Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1978, 43, 1947; Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc. Perkin Trans. 1, 1979, 26; Matsuda, I.; Murata, S.; Izumi, Y. Bull. Chem. Soc. Jpn., 1979, 52, 2389; Corey, E. J.; Chen, Z. Tetrahedron Lett. 1994, 35, 8731; Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511; Fischer, M.-R.; Kirschning, A.; Michel, T.; Schaumann, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 217. 1,4-Migration of silicon from oxygen to carbon has been reported. Marumoto, S.; Kuwajima, I. J. Am. Chem. Soc. 1993, 115, 9021; Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270; Winter, E.; Brückner, R. Synlett 1994, 1049.
44. As shown in Scheme 6, the reaction of 2a with 1,2-epoxypropane in ether gave the unrearranged product 16b after quenching with methanol.
45. LaLonde, R. T.; Ferrara, P. B.; Debboli, Jr. A. D. J. Org. Chem. 1972, 37, 1094.