title: Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach.
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).
authors.affiliation: Centre for Sustainable Chemical Processes, Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK. andy.whiting@durham.ac.uk.
authors.forename: Adam D J
authors.initials: AD
authors.lastname: Calow
authors.forename: Elena
authors.initials: E
authors.lastname: Fernández
authors.forename: Andrew
authors.initials: A
authors.lastname: Whiting
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D000068736:Duloxetine Hydrochloride; D005473:Fluoxetine / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007097:Imines; D013876:Thiophenes; D005473:Fluoxetine; D000068736:Duloxetine Hydrochloride