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

Identifier:  imarina:9440136

Handle: https://hdl.handle.net/20.500.11797/imarina9440136

Authors:  Calow, Adam D J; Fernandez, Elena; Whiting, Andrew

Abstract:
We report efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from alpha,beta-unsaturated aldehydes conducting five sequential one-pot steps (imine formation/copper mediated beta-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).