A versatile tandem retro-[ 1,4]-Brook rearrangement-condensation reaction of o-bromoacetophenone silyl enol ethers

Tetrahedron Letters

Volumn 40, Issue 29, 1999, Pages 5283-5286

  Comanita, Bogdan M ^a,b   Woo, Simon ^a   Fallis, Alex G ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; AROMATIC COMPOUND; OXYGEN; PHENACYL BROMIDE DERIVATIVE; SILANE DERIVATIVE; SILICON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033575429     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00963-6     Document Type: Article

References (30)

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2. (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G.; Legrow, G. E.; MacRae, D. M. Can. J. Chem. 1967, 45, 239. (c) Brook, A. G.; Warner, M. C; Limburg, W. W. Can. J. Chem. 1967, 45, 1231. (d) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (e) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, p. 149.
3. (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G.; Legrow, G. E.; MacRae, D. M. Can. J. Chem. 1967, 45, 239. (c) Brook, A. G.; Warner, M. C; Limburg, W. W. Can. J. Chem. 1967, 45, 1231. (d) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (e) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, p. 149.
4. (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G.; Legrow, G. E.; MacRae, D. M. Can. J. Chem. 1967, 45, 239. (c) Brook, A. G.; Warner, M. C; Limburg, W. W. Can. J. Chem. 1967, 45, 1231. (d) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (e) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, p. 149.
5. (a) Brook, A. G. J. Am. Chem. Soc. 1958, 80, 1886. (b) Brook, A. G.; Legrow, G. E.; MacRae, D. M. Can. J. Chem. 1967, 45, 239. (c) Brook, A. G.; Warner, M. C; Limburg, W. W. Can. J. Chem. 1967, 45, 1231. (d) Brook, A. G. Acc. Chem. Res. 1974, 7, 77. (e) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 2, p. 149.
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8. (a) West, R.; Lowe, R.; Stewart, H. F.; Wright, A. J. Am. Chem. Soc. 1971, 93, 282. (b) West, R.; Wright, A. J. Am. Chem. Soc. 1974, 96, 3214. (c) Evans, D. A.; Takacs, J. M.; Hurst, K. M. J. Am. Chem. Soc. 1979, 101, 371. (d) Eisch, J. J.; Tsai, M. R. J. Organomet. Chem. 1982, 225, 5. (e) Linderman, R. J.; Ghannam, A. J. J. Am. Chem. Soc. 1990, 112, 2392.
9. (a) West, R.; Lowe, R.; Stewart, H. F.; Wright, A. J. Am. Chem. Soc. 1971, 93, 282. (b) West, R.; Wright, A. J. Am. Chem. Soc. 1974, 96, 3214. (c) Evans, D. A.; Takacs, J. M.; Hurst, K. M. J. Am. Chem. Soc. 1979, 101, 371. (d) Eisch, J. J.; Tsai, M. R. J. Organomet. Chem. 1982, 225, 5. (e) Linderman, R. J.; Ghannam, A. J. J. Am. Chem. Soc. 1990, 112, 2392.
10. (a) West, R.; Lowe, R.; Stewart, H. F.; Wright, A. J. Am. Chem. Soc. 1971, 93, 282. (b) West, R.; Wright, A. J. Am. Chem. Soc. 1974, 96, 3214. (c) Evans, D. A.; Takacs, J. M.; Hurst, K. M. J. Am. Chem. Soc. 1979, 101, 371. (d) Eisch, J. J.; Tsai, M. R. J. Organomet. Chem. 1982, 225, 5. (e) Linderman, R. J.; Ghannam, A. J. J. Am. Chem. Soc. 1990, 112, 2392.
11. (a) West, R.; Lowe, R.; Stewart, H. F.; Wright, A. J. Am. Chem. Soc. 1971, 93, 282. (b) West, R.; Wright, A. J. Am. Chem. Soc. 1974, 96, 3214. (c) Evans, D. A.; Takacs, J. M.; Hurst, K. M. J. Am. Chem. Soc. 1979, 101, 371. (d) Eisch, J. J.; Tsai, M. R. J. Organomet. Chem. 1982, 225, 5. (e) Linderman, R. J.; Ghannam, A. J. J. Am. Chem. Soc. 1990, 112, 2392.
12. Wittig, G.; Lhmann, L. Justus Liebigs Ann. Chem. 1942, 550, 260.
13. Bailey, W. F.; Jiang, X.-L. Organometallics 1995, 14, 5704.
14. For 1,3-C to -O and 1,3-O to -C migrations see (a) He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905. (b) Alberti, A.; Chatgilialoglu, C.; Pedulli, G. F.; Zanirato, P. J. Am. Chem. Soc. 1986, 108, 4993. (c) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951. (d) Damrauer, R.; Eaborn, C.; Happer, D. A. R.; Mansour, A. J. Chem. Spc. Chem. Commun. 1983, 348. (e) Smichen, G.; Pfletschinger, J. Angew. Chem., Int. Ed. Engl. 1976, 15, 428.
15. For 1,3-C to -O and 1,3-O to -C migrations see (a) He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905. (b) Alberti, A.; Chatgilialoglu, C.; Pedulli, G. F.; Zanirato, P. J. Am. Chem. Soc. 1986, 108, 4993. (c) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951. (d) Damrauer, R.; Eaborn, C.; Happer, D. A. R.; Mansour, A. J. Chem. Spc. Chem. Commun. 1983, 348. (e) Smichen, G.; Pfletschinger, J. Angew. Chem., Int. Ed. Engl. 1976, 15, 428.
16. For 1,3-C to -O and 1,3-O to -C migrations see (a) He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905. (b) Alberti, A.; Chatgilialoglu, C.; Pedulli, G. F.; Zanirato, P. J. Am. Chem. Soc. 1986, 108, 4993. (c) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951. (d) Damrauer, R.; Eaborn, C.; Happer, D. A. R.; Mansour, A. J. Chem. Spc. Chem. Commun. 1983, 348. (e) Smichen, G.; Pfletschinger, J. Angew. Chem., Int. Ed. Engl. 1976, 15, 428.
17. For 1,3-C to -O and 1,3-O to -C migrations see (a) He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905. (b) Alberti, A.; Chatgilialoglu, C.; Pedulli, G. F.; Zanirato, P. J. Am. Chem. Soc. 1986, 108, 4993. (c) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951. (d) Damrauer, R.; Eaborn, C.; Happer, D. A. R.; Mansour, A. J. Chem. Spc. Chem. Commun. 1983, 348. (e) Smichen, G.; Pfletschinger, J. Angew. Chem., Int. Ed. Engl. 1976, 15, 428.
18. For 1,3-C to -O and 1,3-O to -C migrations see (a) He, H.-M.; Fanwick, P. E.; Wood, K.; Cushman, M. J. Org. Chem. 1995, 60, 5905. (b) Alberti, A.; Chatgilialoglu, C.; Pedulli, G. F.; Zanirato, P. J. Am. Chem. Soc. 1986, 108, 4993. (c) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1993, 34, 1951. (d) Damrauer, R.; Eaborn, C.; Happer, D. A. R.; Mansour, A. J. Chem. Spc. Chem. Commun. 1983, 348. (e) Smichen, G.; Pfletschinger, J. Angew. Chem., Int. Ed. Engl. 1976, 15, 428.
19. For 1,4-O to -C and 1,4-C to -O migrations see (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965. (b) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1988, 29, 1247. (c) Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765. (d) Beese, G.; Keay, B. A. Synlett 1991, 33. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (f) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137. (g) Braun, M.; Mahler, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 896. (h) Lautens, M.; Delanghe, P. H. M.; Goa, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Hoffmann, R. W.; Bewersdorf, M. Tetrahedron Lett. 1990, 31, 67. (j) Hoffmann, R. W.; Brüchner, R. Chem. Ber. 1992, 125, 2731.
20. For 1,4-O to -C and 1,4-C to -O migrations see (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965. (b) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1988, 29, 1247. (c) Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765. (d) Beese, G.; Keay, B. A. Synlett 1991, 33. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (f) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137. (g) Braun, M.; Mahler, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 896. (h) Lautens, M.; Delanghe, P. H. M.; Goa, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Hoffmann, R. W.; Bewersdorf, M. Tetrahedron Lett. 1990, 31, 67. (j) Hoffmann, R. W.; Brüchner, R. Chem. Ber. 1992, 125, 2731.
21. For 1,4-O to -C and 1,4-C to -O migrations see (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965. (b) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1988, 29, 1247. (c) Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765. (d) Beese, G.; Keay, B. A. Synlett 1991, 33. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (f) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137. (g) Braun, M.; Mahler, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 896. (h) Lautens, M.; Delanghe, P. H. M.; Goa, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Hoffmann, R. W.; Bewersdorf, M. Tetrahedron Lett. 1990, 31, 67. (j) Hoffmann, R. W.; Brüchner, R. Chem. Ber. 1992, 125, 2731.
22. For 1,4-O to -C and 1,4-C to -O migrations see (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965. (b) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1988, 29, 1247. (c) Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765. (d) Beese, G.; Keay, B. A. Synlett 1991, 33. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (f) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137. (g) Braun, M.; Mahler, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 896. (h) Lautens, M.; Delanghe, P. H. M.; Goa, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Hoffmann, R. W.; Bewersdorf, M. Tetrahedron Lett. 1990, 31, 67. (j) Hoffmann, R. W.; Brüchner, R. Chem. Ber. 1992, 125, 2731.
23. For 1,4-O to -C and 1,4-C to -O migrations see (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965. (b) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1988, 29, 1247. (c) Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765. (d) Beese, G.; Keay, B. A. Synlett 1991, 33. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (f) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137. (g) Braun, M.; Mahler, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 896. (h) Lautens, M.; Delanghe, P. H. M.; Goa, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Hoffmann, R. W.; Bewersdorf, M. Tetrahedron Lett. 1990, 31, 67. (j) Hoffmann, R. W.; Brüchner, R. Chem. Ber. 1992, 125, 2731.
24. For 1,4-O to -C and 1,4-C to -O migrations see (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965. (b) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1988, 29, 1247. (c) Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765. (d) Beese, G.; Keay, B. A. Synlett 1991, 33. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (f) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137. (g) Braun, M.; Mahler, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 896. (h) Lautens, M.; Delanghe, P. H. M.; Goa, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Hoffmann, R. W.; Bewersdorf, M. Tetrahedron Lett. 1990, 31, 67. (j) Hoffmann, R. W.; Brüchner, R. Chem. Ber. 1992, 125, 2731.
25. For 1,4-O to -C and 1,4-C to -O migrations see (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965. (b) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1988, 29, 1247. (c) Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765. (d) Beese, G.; Keay, B. A. Synlett 1991, 33. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (f) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137. (g) Braun, M.; Mahler, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 896. (h) Lautens, M.; Delanghe, P. H. M.; Goa, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Hoffmann, R. W.; Bewersdorf, M. Tetrahedron Lett. 1990, 31, 67. (j) Hoffmann, R. W.; Brüchner, R. Chem. Ber. 1992, 125, 2731.
26. For 1,4-O to -C and 1,4-C to -O migrations see (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965. (b) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1988, 29, 1247. (c) Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765. (d) Beese, G.; Keay, B. A. Synlett 1991, 33. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (f) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137. (g) Braun, M.; Mahler, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 896. (h) Lautens, M.; Delanghe, P. H. M.; Goa, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Hoffmann, R. W.; Bewersdorf, M. Tetrahedron Lett. 1990, 31, 67. (j) Hoffmann, R. W.; Brüchner, R. Chem. Ber. 1992, 125, 2731.
27. For 1,4-O to -C and 1,4-C to -O migrations see (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965. (b) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1988, 29, 1247. (c) Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765. (d) Beese, G.; Keay, B. A. Synlett 1991, 33. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (f) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137. (g) Braun, M.; Mahler, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 896. (h) Lautens, M.; Delanghe, P. H. M.; Goa, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Hoffmann, R. W.; Bewersdorf, M. Tetrahedron Lett. 1990, 31, 67. (j) Hoffmann, R. W.; Brüchner, R. Chem. Ber. 1992, 125, 2731.
28. For 1,4-O to -C and 1,4-C to -O migrations see (a) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1987, 28, 5965. (b) Bures, E. J.; Keay, B. A. Tetrahedron Lett. 1988, 29, 1247. (c) Spinazzé, P. G.; Keay, B. A. Tetrahedron Lett. 1989, 30, 1765. (d) Beese, G.; Keay, B. A. Synlett 1991, 33. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N. J. Org. Chem. 1991, 56, 1914. (f) Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137. (g) Braun, M.; Mahler, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 896. (h) Lautens, M.; Delanghe, P. H. M.; Goa, J. B.; Zhang, C. H. J. Org. Chem. 1995, 60, 4213. (i) Hoffmann, R. W.; Bewersdorf, M. Tetrahedron Lett. 1990, 31, 67. (j) Hoffmann, R. W.; Brüchner, R. Chem. Ber. 1992, 125, 2731.
29. For recent syntheses see (a) Evans, D. A.; Wood, M. R.; Trotteer, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700. (b) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708.
30. For recent syntheses see (a) Evans, D. A.; Wood, M. R.; Trotteer, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 2700. (b) Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2708.