Abstract
Exposure of dihydropyridinone 1 to the arylbismuth(V) reagent ( p-F-Ph) 3BiCl 2 in the presence of substoichiometric quantities of tributylphosphine (10 mol %) results in aryl transfer to the transiently generated (β-phosphonio)enolate to provide the α-arylated enone 2. This transformation, which represents a regiochemical complement to the Mizoroki–Heck arylation, is used strategically in concise formal and enantioselective total syntheses of the blockbuster antidepressant (−)-paroxetine (PAXIL).
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