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Reviews: (a) Doyle, M. P. Comprehensive Organometallic Chemistry II, Hegedus, L. S., ed., Pergamon Press: New York, 1995; Volume 12, Chap. 5.2. (b) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl., 1994, 33, 1797, (c) Ye, T.; Mckervey, M. A. Chem. Rev. 1994, 94, 1091. (d) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (e) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. (f) Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds., Pergamon Press: New York, 1991; Volume 3, Chapter 4.2. (g) Doyle, M. P. Chem. Rev. 1986, 86, 919.
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For example: (a) Paquette, L. A.; Wang, T.-Z.; Sivik, M. J. Am. Chem. Soc. 1994, 110, 11323. (b) Takano, S.; Yonaga, M.; Morimoto, M.; Ogasawara, K. J. Chem. Soc., Perkin Trans. 1, 1985, 305 and references cited therein. (c) Robin, J. P.; Gringore, O.; Brown, E. Tetrahedron Lett. 1980, 21, 2709. (d) Tomioka, T.; Kawasaki, H.; Iitaka, Y. Tetrahedron Lett. 1985, 26, 903. (e) Hanessian, S.; Murray, P. J.; Sahoo, S. P. Tetrahedron Lett. 1985, 26, 5623 and 5627. (f) Review of related works: Rao, Y. S. Chem Rev. 1976, 76, 625.
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For example: (a) Paquette, L. A.; Wang, T.-Z.; Sivik, M. J. Am. Chem. Soc. 1994, 110, 11323. (b) Takano, S.; Yonaga, M.; Morimoto, M.; Ogasawara, K. J. Chem. Soc., Perkin Trans. 1, 1985, 305 and references cited therein. (c) Robin, J. P.; Gringore, O.; Brown, E. Tetrahedron Lett. 1980, 21, 2709. (d) Tomioka, T.; Kawasaki, H.; Iitaka, Y. Tetrahedron Lett. 1985, 26, 903. (e) Hanessian, S.; Murray, P. J.; Sahoo, S. P. Tetrahedron Lett. 1985, 26, 5623 and 5627. (f) Review of related works: Rao, Y. S. Chem Rev. 1976, 76, 625.
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For example: (a) Paquette, L. A.; Wang, T.-Z.; Sivik, M. J. Am. Chem. Soc. 1994, 110, 11323. (b) Takano, S.; Yonaga, M.; Morimoto, M.; Ogasawara, K. J. Chem. Soc., Perkin Trans. 1, 1985, 305 and references cited therein. (c) Robin, J. P.; Gringore, O.; Brown, E. Tetrahedron Lett. 1980, 21, 2709. (d) Tomioka, T.; Kawasaki, H.; Iitaka, Y. Tetrahedron Lett. 1985, 26, 903. (e) Hanessian, S.; Murray, P. J.; Sahoo, S. P. Tetrahedron Lett. 1985, 26, 5623 and 5627. (f) Review of related works: Rao, Y. S. Chem Rev. 1976, 76, 625.
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For example: (a) Paquette, L. A.; Wang, T.-Z.; Sivik, M. J. Am. Chem. Soc. 1994, 110, 11323. (b) Takano, S.; Yonaga, M.; Morimoto, M.; Ogasawara, K. J. Chem. Soc., Perkin Trans. 1, 1985, 305 and references cited therein. (c) Robin, J. P.; Gringore, O.; Brown, E. Tetrahedron Lett. 1980, 21, 2709. (d) Tomioka, T.; Kawasaki, H.; Iitaka, Y. Tetrahedron Lett. 1985, 26, 903. (e) Hanessian, S.; Murray, P. J.; Sahoo, S. P. Tetrahedron Lett. 1985, 26, 5623 and 5627. (f) Review of related works: Rao, Y. S. Chem Rev. 1976, 76, 625.
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See Supporting Information.
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For discussion on the dramatic influence of solvent polarity on the chemoselectivity of the Rh(II) carbenoid-mediated reaction, see (a) Davies, H. M. L.; Matasi, J. J.; Ahmed, G. J. Org. Chem. 1996, 61, 2305. (b) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696 and references cited therein.
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and references cited therein
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For discussion on the dramatic influence of solvent polarity on the chemoselectivity of the Rh(II) carbenoid-mediated reaction, see (a) Davies, H. M. L.; Matasi, J. J.; Ahmed, G. J. Org. Chem. 1996, 61, 2305. (b) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696 and references cited therein.
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85088543811
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4 favored insertion into tertiary C-H bond
-
4 favored insertion into tertiary C-H bond,
-
-
-
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42
-
-
0023742849
-
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4 was also found to favor cyclopropanation reaction, see (i) Sundberg, R. J.; Baxter, E. W.; Pitts, W. J.; Ahmed-Schofield, R.; Nishiguchi, T. J. Org. Chem. 1988, 53, 5097. (ii) Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssie, P. J. Org. Chem. 1980, 45, 695. (iii) Hubert, A. J.; Noels, A. F.; Anciaux, A. J.; Teyssie, P. Synthesis 1976, 600.
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4544328336
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4 was also found to favor cyclopropanation reaction, see (i) Sundberg, R. J.; Baxter, E. W.; Pitts, W. J.; Ahmed-Schofield, R.; Nishiguchi, T. J. Org. Chem. 1988, 53, 5097. (ii) Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssie, P. J. Org. Chem. 1980, 45, 695. (iii) Hubert, A. J.; Noels, A. F.; Anciaux, A. J.; Teyssie, P. Synthesis 1976, 600.
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4 was also found to favor cyclopropanation reaction, see (i) Sundberg, R. J.; Baxter, E. W.; Pitts, W. J.; Ahmed-Schofield, R.; Nishiguchi, T. J. Org. Chem. 1988, 53, 5097. (ii) Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssie, P. J. Org. Chem. 1980, 45, 695. (iii) Hubert, A. J.; Noels, A. F.; Anciaux, A. J.; Teyssie, P. Synthesis 1976, 600.
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45
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1542457006
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note
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Diazo compounds in which the ethyl group in 2a,b was replaced with a 3,4-dimethoxyphenyl moiety were also prepared. The Rh(II)-catalyzed reaction in 2a resulted in an intractable mixture of products whereas in 2b there was a marked decrease in the regio- and chemoselectivities of the reaction. A complex mixture of products, such as those that had resulted from tertiary C-H insertion, aromatic substitution and cycloaddition, were obtained.
-
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47
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84981407200
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