Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 17, Pages 6838-6840Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8010705
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Funding
- Natural Science and Engineering Research Council of Canada (NSERC)
- Merck Frosst Canada Ltd.
- Boehringer Ingelheim (Canada), Ltd.
- Canada Research Chairs Program
- Canadian Foundation for Innovation
- Universite de Montreal
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Nucleophilic ring opening of methyl 1-nitrocyclopropanecarboxylates by phenol derivatives in the presence Of Cs(2)CO(3) 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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