Nucleophilic addition of phenol derivatives to methyl 1-nitrocyclopropanecarboxylates |
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Authors: | Lifchits Olga Alberico Dino Zakharian Irina Charette André B |
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Institution: | Department of Chemistry, Université de Montréal, P. O. 6128, Station Downtown, Montréal, Quebec, Canada H3C 3J7. |
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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). |
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