Nucleophilic Addition of Phenol Derivatives to Methyl 1-Nitrocyclopropanecarboxylates
| Autor: | Dino Alberico, Irina Zakharian, Olga Lifchits, André B. Charette |
|---|---|
| Rok vydání: | 2008 |
| Předmět: |
Cyclopropanes
Nucleophilic addition Adrenergic Uptake Inhibitors Propylamines Organic Chemistry Carbonates Enantioselective synthesis Cesium Stereoisomerism Alcohol Atomoxetine Hydrochloride Nitro Compounds Methylation Chemical synthesis Cyclopropane chemistry.chemical_compound Models Chemical Phenols chemistry Nucleophile Organic chemistry Phenol Enantiomeric excess |
| Zdroj: | The Journal of Organic Chemistry. 73:6838-6840 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | Nucleophilic ring opening of methyl 1-nitrocyclopropanecarboxylates by phenol derivatives in the presence of Cs2CO3 is described. The reaction tolerates a variety of substituents on both the aromatic alcohol and the cyclopropane and affords the products in good yields (53-84%) and with complete preservation of the enantiomeric excess at C-4. The methodology was applied in an enantioselective synthesis of the norepinephrine reuptake inhibitor atomoxetine (Strattera). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|