949568-47-2

Upstream product

• 501426-95-5 methyl (E,4R)-4-(2,5-cyclohexadienyl)-4-(3,4-dichlorophenyl)-2-butenoate 
• 6287-38-3 3,4-dichlorobenzaldehyde 
• 1198097-83-4 (E)-methyl 3-(3,4-dichlorophenyl)-3-phenylacrylate 
• 405-02-7 1,2-dichloro-4-diazoniumbenzene tetrafluoroborate 
• 103-26-4 Methyl cinnamate 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 79175-35-2 3,4-dichlorophenylmagnesium bromide 
• 234084-70-9 methyl (E)-2-diazo-4-(3,4-dichlorophenyl)-3-butenoate 
• 127404-77-7 (E)-4-(3,4-dichlorophenyl)but-3-enoic acid 
• 949568-31-4 (R)-1,2-dichloro-4-(1-phenylallyl)benzene 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 304021-48-5 methyl (4R)-4-(3,4-dichlorophenyl)-4-phenylbutanoate 
• 147255-16-1 (4R)-4-(3,4-dichlorophenyl)-4-phenylbutanoic acid 
• 124379-29-9 (4S)-4-(3,4-dichlorophenyl)-1-tetralone 
• 155748-61-1 (4R)-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone 

Relevant academic research and scientific papers

Two stereocentered HKR of anti -β,β′-diphenylpropanoxirane and anti -3-phenylethyloxiranes catalysed by Co(iii)(salen)-OAc complex: Enantioselective synthesis of (+)-sertraline and (+)-naproxen

The Co(III)(salen)OAc-catalyzed two stereocentered hydrolytic kinetic resolution (HKR) of anti-β,β′-diphenylmethyloxirane and anti-3-phenylethyloxiranes affords the corresponding anti-1,2-diols and oxiranes in high enantiomeric excess. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of (+)-sertraline, an antidepressant drug, and (+)-naproxen, an anti-inflammatory drug.

Enantioselective iridium-catalyzed allylic arylation

We describe herein the development of the first iridium-catalyzed allylic substitution using arylzinc nucleophiles. High enantioselectivities were obtained from the reactions, which used commercially available Grignard reagents as the starting materials. This methodology was also shown to be compatible with halogen/metal exchange reactions. Its synthetic potential is demonstrated by its application towards the formal synthesis of (+)-sertraline.

Iridium-catalyzed asymmetric allylic substitution with aryl zinc reagents

Thanks to iridium catalysis, arylzinc reagents undergo regioselective allylic substitution with very high enantioselectivity, when associated with phosphoramidite ligands.

Catalytic asymmetric synthesis of diarylacetates and 4,4-diarylbutanoates. A formal asymmetric synthesis of (+)-sertraline

(equation presented) The intermolecular C-H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N-(dodecylbenzenesulfonyl)prolinate) (Rh2(S-DOSP)4) can be effectively carried out on cyclohexadienes, leading to the asymmetric synthesis of diarylacetates. The reaction of vinyldiazoacetates with cyclohexadienes results in an unprecedented carbenoid reaction that is formally a combined C-H insertion/Cope rearrangement. The synthetic utility of this novel transformation was demonstrated by its utilization in a formal asymmetric synthesis of (+)-sertraline.