title: Nucleophilic addition of phenol derivatives to methyl 1-nitrocyclopropanecarboxylates.
abstract: 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).
authors.affiliation: Department of Chemistry, Université de Montréal, P. O. 6128, Station Downtown, Montréal, Quebec, Canada H3C 3J7.
authors.forename: Olga
authors.initials: O
authors.lastname: Lifchits
authors.forename: Dino
authors.initials: D
authors.lastname: Alberico
authors.forename: Irina
authors.initials: I
authors.lastname: Zakharian
authors.forename: André B
authors.initials: AB
authors.lastname: Charette
mesh_terms: D018759:Adrenergic Uptake Inhibitors / Q000138:chemical synthesis*; D000069445:Atomoxetine Hydrochloride; D002254:Carbonates / Q000737:chemistry; D002586:Cesium / Q000737:chemistry; D003521:Cyclopropanes / Q000138:chemical synthesis*; D008745:Methylation; D008956:Models, Chemical; D009574:Nitro Compounds / Q000138:chemical synthesis*; D010636:Phenols / Q000737:chemistry*; D011437:Propylamines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D018759:Adrenergic Uptake Inhibitors; D002254:Carbonates; D003521:Cyclopropanes; D009574:Nitro Compounds; D010636:Phenols; D011437:Propylamines; C015766:cyclopropanecarboxylic acid; D002586:Cesium; D000069445:Atomoxetine Hydrochloride