Enantioselective palladium(0)-catalyzed Nazarov-type cyclization
| Autor: | Craig Stewart, Abdurrahman C. Atesin, Kei Kitamura, Naoyuki Shimada, Marcus A. Tius, Tülay A. Ateşin |
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| Rok vydání: | 2015 |
| Předmět: |
Phosphoramidite
Stereochemistry Aryl Methanol Enantioselective synthesis Diastereomer chemistry.chemical_element Dioxolanes Stereoisomerism General Medicine General Chemistry Cyclopentanes Catalysis Stereocenter chemistry.chemical_compound chemistry Cyclization Pyridine Enantiomeric excess Palladium |
| Zdroj: | Angewandte Chemie (International ed. in English). 54(21) |
| ISSN: | 1521-3773 |
| Popis: | A Pd(0)-catalyzed asymmetric Nazarov-type cyclization is described. The optimized ligand for the reaction incorporates a weakly coordinating pyridine ring into a TADDOL-derived phosphoramidite (TADDOL=α,α,α,α-tetraaryl-1,3-dioxolane-4,5-dimethanol). The reaction leads to the formation of cyclopentenones as single diastereoisomers that incorporate two contiguous asymmetric centers, one tertiary and one an all-carbon-atom quaternary stereocenter, in high yield and optical purity. It is noteworthy that the reaction does not require that substrates should be activated by aryl substituents. |
| Databáze: | OpenAIRE |
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