Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach?

Organic & Biomolecular Chemistry Pub Date: 2014-07-03 DOI: 10.1039/C4OB01142B

Abstract

We report efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from α,β-unsaturated aldehydes conducting five sequential one-pot steps (imine formation/copper mediated β-borylation/transimination/reduction/oxidation) followed by the specific ether group formation which deliver the desired products (R)-fluoxetine in 45% yield (96% ee) and (S)-duloxetine in 47% yield (94% ee).

Graphical abstract: Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach
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