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Initial studies on the synthesis of the diene framework by Diels-Alder cycloaddition of dienes to alkyne-based dieneophiles were discontinued because only moderate enantioselectivities were observed.
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73949099296
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Use of 1.0 equiv of KOH is optimal for reactions promoted by Rh-6.
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Use of 1.0 equiv of KOH is optimal for reactions promoted by Rh-6.
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28
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84868072042
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Diels-Alder cycloaddition promoted by 2 between β-chloroacrylate 1 and 1,3-cyclohexadiene (24 °C) results in <2% conversion.
-
Diels-Alder cycloaddition promoted by 2 between β-chloroacrylate 1 and 1,3-cyclohexadiene (24 °C) results in <2% conversion.
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-
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31
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84868072907
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2, 24 °C).
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2, 24 °C).
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32
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73949143600
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In select cases, Rh-12 is significantly more selective than Rh-11. For example, the reaction presented in Table 4, entry 4 promoted by Rh-11 furnishes the product with 75% ee.
-
In select cases, Rh-12 is significantly more selective than Rh-11. For example, the reaction presented in Table 4, entry 4 promoted by Rh-11 furnishes the product with 75% ee.
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-
-
-
33
-
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73949158330
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For reactions promoted by Rh-12, in general, use of MeOH leads to slightly higher levels of enantioselectivity versus dioxane. For reactions presented in Table 2, MeOH was found to provide similar results as dioxane.
-
For reactions promoted by Rh-12, in general, use of MeOH leads to slightly higher levels of enantioselectivity versus dioxane. For reactions presented in Table 2, MeOH was found to provide similar results as dioxane.
-
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34
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0000579381
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