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For examples of aryl migration, see: (a) Witkop, B, Ek, A. J. Am. Chem. Soc. 1951, 73, 5664
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For examples of aryl migration, see: (a) Witkop, B.; Ek, A. J. Am. Chem. Soc. 1951, 73, 5664.
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8
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33646786647
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10
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and references cited therein. For elegant examples, please see: a
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For elegant examples, please see: (a) Williams, R. M.; Cox, R. J. Acc. Chem. Res. 2003, 36, 127, and references cited therein.
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(d) Lachia, M.; Poriel, C.; Slawin, A. M. Z.; Moody, C. J. Chem. Commun. 2007, 286.
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Lachia, M.1
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Gushing, T.D.1
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Williams, R.M.3
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23
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61349161454
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While control experiments revealed no product inhibition by either the indoxyl or the oxindole products, we prefer the use of stoichiometric quantities of scandium trifluoromethanesulfonate to accelerate the overall rate of conversion to the desired product compare entries 8 and 9, Table 1
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While control experiments revealed no product inhibition by either the indoxyl or the oxindole products, we prefer the use of stoichiometric quantities of scandium trifluoromethanesulfonate to accelerate the overall rate of conversion to the desired product (compare entries 8 and 9, Table 1).
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24
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0026733301
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For an important observation with a dialkyl indoxyl, see: a
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For an important observation with a dialkyl indoxyl, see: (a) Güller, R.; Borscheberg, H. Tetrahedron: Asymmetry 1992, 3, 1197.
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Tetrahedron: Asymmetry
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Güller, R.1
Borscheberg, H.2
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25
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0028344381
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2) led to decomposition.
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2) led to decomposition.
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27
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0025324468
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For 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide, see: Davis, F. A.; Towson, J. C.; Vashi, D. B.; ThimmaReddy, R.; McCauley, J. P., Jr.; Harakal, M. E.; Gosciniak, D. J. J. Org. Chem. 1990, 55, 1254. Use of this reagent generally resulted in cleaner reaction mixtures than those observed with in situ generated DMDO.
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For 3-n-butyl-1,2-benzisothiazole-1,1-dioxide oxide, see: Davis, F. A.; Towson, J. C.; Vashi, D. B.; ThimmaReddy, R.; McCauley, J. P., Jr.; Harakal, M. E.; Gosciniak, D. J. J. Org. Chem. 1990, 55, 1254. Use of this reagent generally resulted in cleaner reaction mixtures than those observed with in situ generated DMDO.
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28
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34249106749
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(a) Grubbs, A. W.; Artraan, G. D.; Tsukamoto, S.; Williams, R. M. Angew. Chem., Int. Ed. 2007, 46, 2257.
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Grubbs, A.W.1
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29
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0032125820
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(b) He, F.; Foxman, B. M.; Snider, B. B. J. Am. Chem. Soc. 1998, 120, 6417.
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He, F.1
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Scheidt, K. A.; Chen, H.; Follows, B. C.; Chemler, S. R.; Coffey, D. S.; Roush, W. R. J. Org. Chem. 1998, 63, 6436.
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Scheidt, K.A.1
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Chemler, S.R.4
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Roush, W.R.6
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34
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61349195547
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Shortening of the reaction time to 1 h led to isolation of the desired 4e along with the corresponding 2-(7-indolyl)-2-(2-phthalimido-ethyl) indoxyl (S6e) in 97% yield (4e:S6e, 84:16).
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Shortening of the reaction time to 1 h led to isolation of the desired 4e along with the corresponding 2-(7-indolyl)-2-(2-phthalimido-ethyl) indoxyl (S6e) in 97% yield (4e:S6e, 84:16).
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35
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61349115925
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Please see Supporting Information for details
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Please see Supporting Information for details.
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36
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38349112828
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and references therein. For representative examples, see: a
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For representative examples, see: (a) Colby Davie, E. A.; Mennen, S. M.; Xu, Y.; Miller, S. J. Chem. Rev. 2007, 107, 5759, and references therein.
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Colby Davie, E.A.1
Mennen, S.M.2
Xu, Y.3
Miller, S.J.4
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84989536113
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(c) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
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Jacobsen, E.N.1
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Ecker, J.R.4
Deng, L.5
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