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0029763545
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3Al reaction with disubstituted 2,3-epoxy-1-ols, see: (a) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata. M.; Tachibana, K.; Yasumoto, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 1672.
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(b) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Ibid. 1996, 35, 1675.
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(f) Hazra, B. G.; Joshi, P. L.; Bahule, B. B.; Argade, N. P.; Pore, V. S.; Chordia, M. D. Tetrahedron 1994, 50, 2523.
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(g) Ojika, M.; Kigoshi, H.; Ishigaki, T.; Nisiwaki, M.; Tsukada, I.; Mizuta, K.; Yamada, K. Tetrahedron Lett. 1993, 34, 8505.
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(i) Iguchi, K.; Fujita, M.; Nagaoka, H.; Mitome, H.; Yamada, Y. Ibid. 1993, 34, 6277.
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(j) Hale, K. J.; Bhatia, G. S.; Peak, S. A.; Manaviazar, S. Ibid. 1993, 34, 5343.
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(k) Romo, D.; Johnson, D. D.; Plamondon, L.; Miwa, T.; Schreiber, S. L. J. Org. Chem. 1992, 57, 5060.
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3Al-promoted methylation-ring opening of a trisubstituted epoxide at the less substituted position, see: Honda, T.; Tomitsuka, K.; Tsubuki, M. J. Org. Chem. 1993, 58, 4274.
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0029937840
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For analogous examples of epoxide neighboring group 1,2-migration, see: (a) Kita, Y.; Kitagaki, S.; Imai, R.; Okamoto, S.; Mihara, S.; Yoshida, Y.; Akai, S.; Fujioka, H. Tetrahedron Lett. 1996, 37, 1817.
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26
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0028265116
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0012503108
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1,2-Hydride migration in the reaction of disubstituted 2,3-epoxy-1-ols has been shown to occur on treatment with trialkylaluminum reagents when the resultant carbocation species has similar or greater stability than the initial chelated species; see: Honda, M.; Igarashi, T.; Marubayashi, N.; Komori, T. Liebigs Ann. Chem. 1991, 595.
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0342728112
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note
-
1H-NMR downfield shifts of the hydroxymethyl methylene protons in both isomers; however, only one isomer exhibited a spin-spin coupling of the shifted methylene to the vinyl proton. This isomer was assigned the structure that corresponded to the acetate derived from alcohol 25.
-
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-
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35
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18844410382
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Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
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-
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0343162729
-
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note
-
The diastereomeric purities of Mosher ester derivatives were measured using a DNBPG chiral bonded HPLC column (5 micron) available from J. T. Baker Research Products, Phillipsburg, N. J.
-
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38
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0010640653
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(b) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
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0343598075
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note
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Literature precedent suggests the reaction proceeds via anti-opening of the epoxide (references 7-10).
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0342728094
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note
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Isolated as a 1:1 mixture of E and Z isomers.
-
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45
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0000770827
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