Enhanced stereoselectivity in the capture of a 5-substituted 2-adamantyl radical by substitution of C-5 by negative boron

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9588-9590

  Gonikberg, Elena M ^a   Picart, Francis ^a   Le Noble, William J ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009474189     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9616670     Document Type: Article

References (32)

1. (a) As in all of our previous papers on this subject, we have for the sake of the reader's convenience used the numbering system shown in 1, which in fact applies to adamantanone but which is incorrect for some of the compounds described here; 9-H is actually the pyridine complex of 1- rather than of 5-boraadamantane, for example.
2. (b) Note that with boron lower in priority than carbon, 8 must be designated the Z-isomer.
3. Examples include: (a) Dekkers, A. W. J. D.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1973, 29, 1691. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447. (c) le Noble, W. J.; Chiou, D.-M.; Maluszynska, H.; Okaya, Y. Tetrahedron Lett. 1977, 3865. (d) Grob, C. A.; Wang, G.; Yang, C. Tetrahedron Lett. 1987, 28, 1247. (e) Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5875. (f) Adcock, W.; Coope, J.; Shiner, V. J.; Trout, N. A. J. Org. Chem. 1990, 55, 1411. (g) Burgess, K.; van der Donk, W. A.; Jarstfer, M. B.; Ohlmeyer, M. J. J. Am. Chem. Soc. 1991, 113, 6139. (h) Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017. (i) Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418. (j) Chung, W.-S.; Wang, N.-J.; Liu, Y.-D.; Leu, Y.-J.; Chiang, M. Y. J. Chem. Soc., Perkin Trans. 2 1995, 307.
4. Examples include: (a) Dekkers, A. W. J. D.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1973, 29, 1691. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447. (c) le Noble, W. J.; Chiou, D.-M.; Maluszynska, H.; Okaya, Y. Tetrahedron Lett. 1977, 3865. (d) Grob, C. A.; Wang, G.; Yang, C. Tetrahedron Lett. 1987, 28, 1247. (e) Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5875. (f) Adcock, W.; Coope, J.; Shiner, V. J.; Trout, N. A. J. Org. Chem. 1990, 55, 1411. (g) Burgess, K.; van der Donk, W. A.; Jarstfer, M. B.; Ohlmeyer, M. J. J. Am. Chem. Soc. 1991, 113, 6139. (h) Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017. (i) Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418. (j) Chung, W.-S.; Wang, N.-J.; Liu, Y.-D.; Leu, Y.-J.; Chiang, M. Y. J. Chem. Soc., Perkin Trans. 2 1995, 307.
5. Examples include: (a) Dekkers, A. W. J. D.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1973, 29, 1691. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447. (c) le Noble, W. J.; Chiou, D.-M.; Maluszynska, H.; Okaya, Y. Tetrahedron Lett. 1977, 3865. (d) Grob, C. A.; Wang, G.; Yang, C. Tetrahedron Lett. 1987, 28, 1247. (e) Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5875. (f) Adcock, W.; Coope, J.; Shiner, V. J.; Trout, N. A. J. Org. Chem. 1990, 55, 1411. (g) Burgess, K.; van der Donk, W. A.; Jarstfer, M. B.; Ohlmeyer, M. J. J. Am. Chem. Soc. 1991, 113, 6139. (h) Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017. (i) Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418. (j) Chung, W.-S.; Wang, N.-J.; Liu, Y.-D.; Leu, Y.-J.; Chiang, M. Y. J. Chem. Soc., Perkin Trans. 2 1995, 307.
6. Examples include: (a) Dekkers, A. W. J. D.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1973, 29, 1691. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447. (c) le Noble, W. J.; Chiou, D.-M.; Maluszynska, H.; Okaya, Y. Tetrahedron Lett. 1977, 3865. (d) Grob, C. A.; Wang, G.; Yang, C. Tetrahedron Lett. 1987, 28, 1247. (e) Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5875. (f) Adcock, W.; Coope, J.; Shiner, V. J.; Trout, N. A. J. Org. Chem. 1990, 55, 1411. (g) Burgess, K.; van der Donk, W. A.; Jarstfer, M. B.; Ohlmeyer, M. J. J. Am. Chem. Soc. 1991, 113, 6139. (h) Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017. (i) Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418. (j) Chung, W.-S.; Wang, N.-J.; Liu, Y.-D.; Leu, Y.-J.; Chiang, M. Y. J. Chem. Soc., Perkin Trans. 2 1995, 307.
7. Examples include: (a) Dekkers, A. W. J. D.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1973, 29, 1691. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447. (c) le Noble, W. J.; Chiou, D.-M.; Maluszynska, H.; Okaya, Y. Tetrahedron Lett. 1977, 3865. (d) Grob, C. A.; Wang, G.; Yang, C. Tetrahedron Lett. 1987, 28, 1247. (e) Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5875. (f) Adcock, W.; Coope, J.; Shiner, V. J.; Trout, N. A. J. Org. Chem. 1990, 55, 1411. (g) Burgess, K.; van der Donk, W. A.; Jarstfer, M. B.; Ohlmeyer, M. J. J. Am. Chem. Soc. 1991, 113, 6139. (h) Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017. (i) Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418. (j) Chung, W.-S.; Wang, N.-J.; Liu, Y.-D.; Leu, Y.-J.; Chiang, M. Y. J. Chem. Soc., Perkin Trans. 2 1995, 307.
8. Examples include: (a) Dekkers, A. W. J. D.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1973, 29, 1691. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447. (c) le Noble, W. J.; Chiou, D.-M.; Maluszynska, H.; Okaya, Y. Tetrahedron Lett. 1977, 3865. (d) Grob, C. A.; Wang, G.; Yang, C. Tetrahedron Lett. 1987, 28, 1247. (e) Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5875. (f) Adcock, W.; Coope, J.; Shiner, V. J.; Trout, N. A. J. Org. Chem. 1990, 55, 1411. (g) Burgess, K.; van der Donk, W. A.; Jarstfer, M. B.; Ohlmeyer, M. J. J. Am. Chem. Soc. 1991, 113, 6139. (h) Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017. (i) Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418. (j) Chung, W.-S.; Wang, N.-J.; Liu, Y.-D.; Leu, Y.-J.; Chiang, M. Y. J. Chem. Soc., Perkin Trans. 2 1995, 307.
9. Examples include: (a) Dekkers, A. W. J. D.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1973, 29, 1691. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447. (c) le Noble, W. J.; Chiou, D.-M.; Maluszynska, H.; Okaya, Y. Tetrahedron Lett. 1977, 3865. (d) Grob, C. A.; Wang, G.; Yang, C. Tetrahedron Lett. 1987, 28, 1247. (e) Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5875. (f) Adcock, W.; Coope, J.; Shiner, V. J.; Trout, N. A. J. Org. Chem. 1990, 55, 1411. (g) Burgess, K.; van der Donk, W. A.; Jarstfer, M. B.; Ohlmeyer, M. J. J. Am. Chem. Soc. 1991, 113, 6139. (h) Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017. (i) Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418. (j) Chung, W.-S.; Wang, N.-J.; Liu, Y.-D.; Leu, Y.-J.; Chiang, M. Y. J. Chem. Soc., Perkin Trans. 2 1995, 307.
10. Examples include: (a) Dekkers, A. W. J. D.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1973, 29, 1691. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447. (c) le Noble, W. J.; Chiou, D.-M.; Maluszynska, H.; Okaya, Y. Tetrahedron Lett. 1977, 3865. (d) Grob, C. A.; Wang, G.; Yang, C. Tetrahedron Lett. 1987, 28, 1247. (e) Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5875. (f) Adcock, W.; Coope, J.; Shiner, V. J.; Trout, N. A. J. Org. Chem. 1990, 55, 1411. (g) Burgess, K.; van der Donk, W. A.; Jarstfer, M. B.; Ohlmeyer, M. J. J. Am. Chem. Soc. 1991, 113, 6139. (h) Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017. (i) Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418. (j) Chung, W.-S.; Wang, N.-J.; Liu, Y.-D.; Leu, Y.-J.; Chiang, M. Y. J. Chem. Soc., Perkin Trans. 2 1995, 307.
11. Examples include: (a) Dekkers, A. W. J. D.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1973, 29, 1691. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447. (c) le Noble, W. J.; Chiou, D.-M.; Maluszynska, H.; Okaya, Y. Tetrahedron Lett. 1977, 3865. (d) Grob, C. A.; Wang, G.; Yang, C. Tetrahedron Lett. 1987, 28, 1247. (e) Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5875. (f) Adcock, W.; Coope, J.; Shiner, V. J.; Trout, N. A. J. Org. Chem. 1990, 55, 1411. (g) Burgess, K.; van der Donk, W. A.; Jarstfer, M. B.; Ohlmeyer, M. J. J. Am. Chem. Soc. 1991, 113, 6139. (h) Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017. (i) Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418. (j) Chung, W.-S.; Wang, N.-J.; Liu, Y.-D.; Leu, Y.-J.; Chiang, M. Y. J. Chem. Soc., Perkin Trans. 2 1995, 307.
12. Examples include: (a) Dekkers, A. W. J. D.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1973, 29, 1691. (b) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447. (c) le Noble, W. J.; Chiou, D.-M.; Maluszynska, H.; Okaya, Y. Tetrahedron Lett. 1977, 3865. (d) Grob, C. A.; Wang, G.; Yang, C. Tetrahedron Lett. 1987, 28, 1247. (e) Laube, T.; Stilz, H. U. J. Am. Chem. Soc. 1987, 109, 5875. (f) Adcock, W.; Coope, J.; Shiner, V. J.; Trout, N. A. J. Org. Chem. 1990, 55, 1411. (g) Burgess, K.; van der Donk, W. A.; Jarstfer, M. B.; Ohlmeyer, M. J. J. Am. Chem. Soc. 1991, 113, 6139. (h) Huang, X. L.; Dannenberg, J. J. J. Am. Chem. Soc. 1993, 115, 6017. (i) Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418. (j) Chung, W.-S.; Wang, N.-J.; Liu, Y.-D.; Leu, Y.-J.; Chiang, M. Y. J. Chem. Soc., Perkin Trans. 2 1995, 307.
13. Bodepudi, V.; le Noble, W. J. J. Org. Chem. 1991, 56, 2001.
14. Cheung, C. K.; Tseng, L. T.; Lin, M.-h.; Srivastava, S.; le Noble, W. J. J. Am. Chem. Soc. 1986, 108, 1598; 1987, 109, 7239.
15. Cheung, C. K.; Tseng, L. T.; Lin, M.-h.; Srivastava, S.; le Noble, W. J. J. Am. Chem. Soc. 1986, 108, 1598; 1987, 109, 7239.
16. Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.
17. For references and discussion, see: Lau, J.; Hung, R.; Gonikberg, E. M.; le Noble, W. J. J. Am. Chem. Soc. 1995, 117, 11421.
18. See, for example: Advanced Organic Chemistry, 3rd ed.; Wheland, G. W., Ed.; Wiley: New York, 1960; Chapter 11.
19. An exception has been claimed (not in the adamantane series). See: Wipf, P.; Kim, Y. J. Am. Chem. Soc. 1994, 116, 11678.
20. Adcock, W.; Clark, C. K.; Trout, N. A. Tetrahedron Lett. 1994, 35, 297.
21. See ref 2f and Xie, M.; le Noble, W. J. J. Org. Chem. 1989, 54, 3836 and 3839.
22. Adcock, W.; Cotton, J.; Trout, N. A. J. Org. Chem. 1994, 59, 1867.
23. Hahn, J. M.; le Noble, W. J. J. Am. Chem. Soc. 1992, 114, 1916.
24. Reference 6 and Gonikberg, E. M.; le Noble, W. J. J. Org. Chem. 1995, 60, 7751.
25. (a) Michailov, B. M.; Baryshnikova, T. K. Bull. Acad. Sci. USSR, Chem. Sci. 1979, 1358 and 2361.
26. (b) Michailov, B. M.; Cherkasova, K. L. J. Organomet. Chem. 1983, 246, 9.
27. Greene, F. D.; Lowry, N. N. J. Org. Chem. 1967, 32, 882.
28. Kuivila, H. G. Synthesis 1970, 499.
29. Kira, M.; Akiyama, M.; Ichinose, M.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 8256.
30. Bartlett, P. D.; McBride, J. M. J. Am. Chem. Soc. 1965, 87, 1727. As a reviewer has noted, the comparison is of two reactions in which a different atom is abstracted (bromine by 6 and hydrogen by 7). Unfortunately, 8 is unstable to bromine, and 1-phenyladamantane does not lend itself to the NMR analysis described here. The stereochemistry is not expected to be affected by this difference, however.
31. Gung, B. W.; Wolf, M. A. J. Org. Chem. 1996, 61, 232.
32. Senda, Y.; Morita, M.; Itoh, H. J. Chem. Soc., Perkin Trans. 2 1996, 221.