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Scope, Application and Mechanistic Details of the Nickel-Catalyzed Z-Selective Isomerization of Terminal Olefins
In this dissertation, the mechanism of the nickel-catalyzed Z-selective isomerization of terminal alkenes with the additive diphenylphosphine could be successfully clarified. The nickel-catalyzed Z-selective isomerization of terminal alkenes was successfully applied as key step in the synthesis of t...
में बचाया:
| मुख्य लेखक: | |
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| अन्य लेखक: | |
| स्वरूप: | Dissertation |
| भाषा: | अंग्रेज़ी |
| प्रकाशित: |
Philipps-Universität Marburg
2018
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| विषय: | |
| ऑनलाइन पहुंच: | पीडीएफ पूर्ण पाठ |
| टैग: |
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| सारांश: | In this dissertation, the mechanism of the nickel-catalyzed Z-selective isomerization of terminal alkenes with the additive diphenylphosphine could be successfully clarified. The nickel-catalyzed Z-selective isomerization of terminal alkenes was successfully applied as key step in the synthesis of the pheromone of the beet armyworm spodoptera exigua, (9Z,12Z)-tetradeca-9,12-dien-1-yl acetate (165). For the final isomerization step, Ni(dppe)Cl2 emerged as the pre-catalyst of choice. Regarding the diversification of the substrate scope, secondary and tertiary N-allyl amides and carbamates were well-tolerated. The feature of the method was a substrate-specific isomerization. Secondary amides (and carbamates) predominantly formed the Z-configured enamide (and enecarbamate, respectively), whereas tertiary amides and oxazolidinones gave the E-configured product. The final challenge of the catalyst system was the tolerance towards functional groups, which
were not located in the substrate itself, but additional reactants. According to this, a diastereoselective isomerization/allylboration sequence was realized and up to 96% syn-selectivity could be achieved. |
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| भौतिक वर्णन: | 247 Seiten |
| डिजिटल ऑब्जेक्ट पहचानकर्ता: | 10.17192/z2019.0118 |