949568-31-4

Upstream product

• 79175-35-2 3,4-dichlorophenylmagnesium bromide 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 6287-38-3 3,4-dichlorobenzaldehyde 
• 129140-95-0 C₉H₇BrCl₂ 
• 591-51-5 phenyllithium 
• 85217-69-2 cinnamyl methyl carbonate 
• 1136238-65-7 3-(3,4-dichlorophenyl)allyl methyl carbonate 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 949568-47-2 (R,E)-methyl 4-(3,4-dichlorophenyl)-4-phenylbut-2-enoate 
• 304021-48-5 methyl (4R)-4-(3,4-dichlorophenyl)-4-phenylbutanoate 

Relevant academic research and scientific papers

Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds

A highly enantioselective copper/N-heterocyclic carbene catalyzed allylic arylation with organolithium compounds is presented. The use of commercial or readily prepared aryllithium reagents in the reaction with allyl bromides affords a variety of chiral diarylvinylmethanes, comprising a privileged structural motif in pharmaceuticals, in high yields with good to excellent regio- and enantioselectivities. The versatility of this new transformation is illustrated in the formal synthesis of the marketed drug tolterodine (Detrol).

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.