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Issue 25, 2017
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Stereodivergent synthesis of all the four stereoisomers of antidepressant reboxetine

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Abstract

Chiral amino alcohol–copper(II) catalysts Cu-L1c and Cu-ent-L1c were utilized to promote the diastereoselective nitroaldol reactions of chiral aldehydes (S)-3 or (R)-3 with nitromethane, which respectively led to the preferential formation of certain stereoisomer for nitro diol derivatives 4. Using this catalytic protocol, all the four stereoisomers of the antidepressant reboxetine were divergently prepared. The highest overall yield of this synthetic route reached up to 30.5% from aldehyde (S)-3.

Graphical abstract: Stereodivergent synthesis of all the four stereoisomers of antidepressant reboxetine

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Publication details

The article was received on 25 May 2017, accepted on 07 Jun 2017 and first published on 09 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01283G
Citation: Org. Biomol. Chem., 2017,15, 5395-5401
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    Stereodivergent synthesis of all the four stereoisomers of antidepressant reboxetine

    C. Liu, Z. Lin, Z. Zhou and H. Chen, Org. Biomol. Chem., 2017, 15, 5395
    DOI: 10.1039/C7OB01283G

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