200114-10-9

Upstream product

• 118798-76-8 tris(4-fluorophenyl)bismuth dichloride 
• 94923-25-8 1-benzyl-1,2,3,6-tetrahydropyridin-4-en-3-one 
• 916214-12-5 3-(diphenoxy-phosphoryloxy)-4-(4-fluoro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 916214-13-6 4-(4-fluoro-phenyl)-3-[(isopropoxy-dimethyl-silanyl)-methyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 916214-14-7 4-(4-fluoro-phenyl)-3-hydroxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 916214-01-2 1-benzyl-4-(4-fluoro-phenyl)-1,6-dihydro-2H-pyridin-3-one 
• 916214-03-4 4-(4-fluoro-phenyl)-3-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 916214-11-4 4-(4-fluoro-phenyl)-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester 
• 533-31-3 Sesamol 

Downstream Products

• 61869-08-7 paroxetine 
• 110429-35-1 (-)-paroxetine hydrochloride 

Relevant academic research and scientific papers

Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines

We have developed a novel approach for the synthesis of enantioenriched 3-boryl-tetrahydropyridines via the Cu(I)-catalyzed regio-, diastereo-, and enantioselective protoborylation of 1,2-dihydropyridines, which were obtained by the partial reduction of the pyridine derivatives. This dearomatization/enantioselective borylation stepwise strategy provides facile access to chiral piperidines together with the stereospecific transformation of a stereogenic C-B bond from readily available starting materials. Furthermore, the utility of this method is demonstrated for the concise synthesis of the antidepressant drug (-)-paroxetine. A theoretical study of the reaction mechanism is also described.

Enantioselective total and formal syntheses of paroxetine (PAXIL) via phosphine-catalyzed enone α-arylation using arylbismuth(V) reagents: a regiochemical complement to Heck arylation

Exposure of dihydropyridinone 1 to the arylbismuth(V) reagent (p-F-Ph)3BiCl2 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).