Cross-Metathesis of Methallyl Halides: Concise Enantioselective Formal Total Synthesis of (-)-Presphaerene
| Autor: | Hari Krishna Nallapaneni, Jungjoong Hwang, Jongkook Lee, Jaun Koo, Suresh Mandava, Haeil Park |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Halide
chemistry.chemical_element 02 engineering and technology 010402 general chemistry Metathesis 01 natural sciences Catalysis presphaerene lcsh:Chemistry chemistry.chemical_compound Organic chemistry methallyl halide total synthesis Stewart–Grubbs catalyst Original Research Chemistry Enantioselective synthesis cross-metathesis Total synthesis General Chemistry 021001 nanoscience & nanotechnology 0104 chemical sciences Ruthenium Grubbs' catalyst lcsh:QD1-999 0210 nano-technology Selectivity |
| Zdroj: | Frontiers in Chemistry Frontiers in Chemistry, Vol 8 (2020) |
| ISSN: | 2296-2646 |
| Popis: | The cross-metathesis (CM) of methallyl halides catalyzed using four different ruthenium-based complexes-Grubbs catalyst, Grubbs second-generation catalyst, Hoveyda-Grubbs second-generation catalyst, and Stewart-Grubbs catalyst-was investigated. When methallyl chloride or bromide was reacted with a model substrate containing a benzyl ether group, the Grubbs catalyst, and Grubbs second-generation catalyst did not promote the reaction well. However, the Hoveyda-Grubbs second-generation catalyst and Stewart-Grubbs catalyst afforded the corresponding products in moderate to good yield with moderate E/Z selectivity. Accordingly, several functionalized methallyl halides were prepared by CM. Various functional groups were well-tolerated in this system when the Stewart-Grubbs catalyst was used. To demonstrate the practical utility of our method, methallyl halide CM was successfully employed for the formal total synthesis of a natural product (-)-presphaerene, in which the precursor of the key cyclopentanecarboxylate intermediate was efficiently prepared in three steps. |
| Databáze: | OpenAIRE |
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