Nucleophilic addition of phenol derivatives to methyl 1-nitrocyclopropanecarboxylates.
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).
Lifchits
Olga
O
Department of Chemistry, Université de Montréal, P. O. 6128, Station Downtown, Montréal, Quebec, Canada H3C 3J7.
Alberico
Dino
D
Zakharian
Irina
I
Charette
André B
AB
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
D018759:Adrenergic Uptake Inhibitors; D002254:Carbonates; D003521:Cyclopropanes; D009574:Nitro Compounds; D010636:Phenols; D011437:Propylamines; C015766:cyclopropanecarboxylic acid; D002586:Cesium; D000069445:Atomoxetine Hydrochloride