Issue 25, 2017

Stereodivergent synthesis of all the four stereoisomers of antidepressant reboxetine

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

Supplementary files

Article information

Article type
Paper
Submitted
25 May 2017
Accepted
07 Jun 2017
First published
09 Jun 2017

Org. Biomol. Chem., 2017,15, 5395-5401

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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