439271-80-4

Upstream product

• 37643-54-2 N-[(4-methylbenzene-1-sulfonyl)(phenyl)methyl]formamide 
• 557-20-0 diethylzinc 

Downstream Products

• 694529-64-1 N-[1-(4-nitro-phenyl)-propyl]-formamide 
• 1364683-93-1 (R)-N-(4-((3-(1-(4-(tert-butyl)phenyl)propyl)thioureido)methyl)-2-fluorophenyl)methanesulfonamide 
• 1364683-77-1 (R)-N-(4-((3-(1-(4-(tert-butyl)phenyl)propyl)thioureido)methyl)phenyl)methanesulfonamide 
• 1213091-61-2 (R)-1-(4-(tert-butyl)phenyl)propan-1-amine 
• 694529-70-9 1-[1-(4-amino-phenyl)-propyl]-3-(4-tert-butyl-benzyl)-thiourea 
• 694529-66-3 N-[1-(4-amino-phenyl)-propyl]-formamide 
• 694529-68-5 4-((R)-1-Amino-propyl)-phenylamine 
• 2941-20-0 1-phenylpropylamine 

Relevant academic research and scientific papers

Development of chiral catalysts by asymmetric activation for highly enantioselective diethylzinc addition to imines

Based on the asymmetric activation concept, a library of chiral zinc complexes in situ formed by the combination of diimines derived from chiral 1,2-diphenyl-ethanene-1,2-diamine, BINOL derivatives, and diethylzinc are evaluated in the asymmetric addition of diethylzinc to N-acylimines. In the presence of 10 mol% L3ZnA1, high enantioselectivities and yields were provided for a wide range of aromatic imines in 1,2-dichloroethane at -25 °C.

Catalytic enantioselective addition of organometallic reagents to N-formylimines using monodentate phosphoramidite ligands

(Chemical Equation Presented) The asymmetric synthesis of protected amines via the copper/phosphoramidite-catalyzed addition of organozinc and organoaluminum reagents to N-acylimines, generated in situ from aromatic and aliphatic α-amidosulfones, is reported. High yields of optically active N-formyl-protected amines and enantioselectivities up to 99% were obtained. Under the reaction conditions, partial oxidation of the phosphoramidite ligand to the corresponding phosphoric amide was detected. A preliminary study on the origin and the effect on the catalytic addition reaction is presented.

Discovery of chiral catalysts by asymmetric activation for highly enantioselective diethylzinc addition to imines: Using racemic and achiral diimines as effective activators

A library of chiral zinc complexes formed in situ by the combination of achiral and racemic diimines with 3,3′-di(3,5-ditrifluoromethylphenyl)- BINOL and diethylzinc were evaluated in the asymmetric addition of diethylzinc to N-acylimines. In the presence of 10 mol % of chiral ligand 4 and racemic diimine 5, high enantioselectivities of up to 97% ee and yields of up to 96% were achieved for a wide range of aromatic imines in dichloromethane at -30°C.

The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands

The first highly enantioselective dialkylzinc addition to imines in the presence of catalytic amounts of N,O-ligands is reported. N-formyl-α-(p-tolysulfonyl)benzylamines are the readily available starting materials easily obtained in a one-pot synthesis from benzaldehydes, formamide, and p-tolylsulfinic acid. Upon deprotonation, the sulfinate is eliminated to give the acyl imine. The acyl imines further react with alkylzinc reagents in the presence of catalytic amounts of [2.2]paracyclophane-based N,O-ligands L* yielding the alkylated N-(1-phenylpropyl)formamides with excellent yields and enantioselectivities. Copyright