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For an example of deriving the electrophile from a styrene derivative, see: Niggemann, M.; Bisek, N. Chem.-Eur. J. 2010, 16, 11246-11249.
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For isomerization to a mixture of α, β-and β, γ-enones, see: for Pd
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(d) For isomerization to a mixture of α, β-and β, γ-enones, see: (for Pd) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259-266.
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79851492169
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When hex-3-en-2-one, derived from alcohol 2a, was separately reacted with indole 3h in the presence of either Ru-catalyst 1, In OTf 3, or CSA, both the In-and the CSA-catalyst provided adduct 4h in similar yields and reaction time when compared to the mixture of catalysts. Ru-complex 1, however, did not provide any of adduct 4h
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When hex-3-en-2-one, derived from alcohol 2a, was separately reacted with indole 3h in the presence of either Ru-catalyst 1, In (OTf) 3, or CSA, both the In-and the CSA-catalyst provided adduct 4h in similar yields and reaction time when compared to the mixture of catalysts. Ru-complex 1, however, did not provide any of adduct 4h.
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25
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57549097430
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(a) Trost, B. M.; Maulide, N.; Livingston, R. C. J. Am. Chem. Soc. 2008, 130, 16502-16503.
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27
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79851486112
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In the course of experiments 5 mol % of ruthenium catalyst 1 were found to provide the most reliable results for the RICA reactions
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In the course of experiments 5 mol % of ruthenium catalyst 1 were found to provide the most reliable results for the RICA reactions.
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28
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79851489737
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1H NMR using 4-methoxyacetophenone as an internal standard
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1H NMR using 4-methoxyacetophenone as an internal standard.
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29
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70749115302
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For an example of an asymmetric addition, see:, For nonasymmetric examples, see
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(a) For an example of an asymmetric addition, see: Adachi, S.; Tanaka, F.; Watanabe, K.; Harada, T. Org. Lett. 2009, 11, 5206-5209. For nonasymmetric examples, see:
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Adachi, S.1
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Soriente, A.1
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Scettri, A.6
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0000208326
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In these reported experiments 2-methylfuran was used in large excess 4-5 equiv
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(c) Poirier, J.-M.; Dujardin, G. Heterocycles 1987, 25, 399-407. In these reported experiments 2-methylfuran was used in large excess (4-5 equiv).
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Poirier, J.-M.1
Dujardin, G.2
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