66558-06-3

Upstream product

• 66562-22-9 4-Methyl-benzenesulfinic acid ((S)-1-phenyl-propyl)-amide 
• 942066-19-5 4-methyl-N-[1-phenyl-propylidene]-benzenesulfonamide 
• 557-20-0 diethylzinc 
• 51608-60-7 phenyl N-tosyl imine 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 6873-55-8 p-tolylsulfinyl amide 
• 93-55-0 1-phenyl-propan-1-one 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 100-47-0 benzonitrile 
• 866993-20-6 (S)-4-methyl-N-(1-phenylethylidene)benzenesulfinamide 
• 70-55-3 toluene-4-sulfonamide 

Relevant academic research and scientific papers

The enantioselective diethylzinc addition to imines catalyzed by chiral Cu(II)-oxazoline complexes

A series of copper complexes of chiral bisoxazolines has been applied in the catalytic diethylzinc addition to N-sulfonyl imines. It has been found that the tridentate ligands 3-5 provided higher enantioselectivity than bidentate ones. Addition of 4 A molecular sieves to the reaction system benefits the enantioselectivity. The optimal procedure for diethylzinc addition to different imines resulted in moderate yields and enantioselectivities of up to 82% ee.

Asymmetric Stepwise Reductive Amination of Sulfonamides, Sulfamates, and a Phosphinamide by Nickel Catalysis

Asymmetric reductive amination of poorly nucleophilic sulfonamides was realized in the presence of nickel catalysts and titanium alkoxide. A wide range of ketones, including enolizable ketones and some biaryl ones, were converted into sulfonamides in excellent enantiomeric excess. The cyclization of sulfamates and intermolecular reductive amination of a diarylphosphinamide were also successful. Formic acid was used as a safe and economic surrogate of high-pressure hydrogen gas.

PFAM catalyzed enantioselective diethylzinc addition to imines

Chiral amines are important starting materials for the synthesis of biologically important compounds. Enantioselective addition of dialkylzinc reagents to imines is a reliable method for the synthesis of these compounds. Different chiral catalysts were de

Chiral N-Heterocyclic Carbene Ligands Bearing a Pyridine Moiety for the Copper-Catalyzed Alkylation of N-Sulfonylimines with Dialkylzinc Reagents

Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99 % ee). The addition of HMPA to the reaction mixture as a co-solvent is critical in terms of chemical yield and enantioselectivity. A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction. Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99 % ee; see scheme). A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction.

Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation

Picolinamide-cinchona organocatalysts for the successful enantioselective reduction of ketomines were developed. For the first time, a new type of chiral Lewis base, a cationic species, is reported to efficiently organocatalyze the addition of trichlorosi

Highly enantioselective Rh-catalyzed transfer hydrogenation of N-sulfonyl ketimines

Several imine species comprising N-sulfinyl and N-sulfonyl ketimine, oxime, and enamine derivatives were subjected to asymmetric transfer hydrogenation in an azeotropic mixture of formic acid/triethylamine. Among them, the Rh-catalyzed transfer hydrogenat

Highly enantioselective Pd-catalyzed asymmetric hydrogenation of activated imines

(Chemical Equation Presented) Pd/bisphosphines complexes are highly effective catalysts for asymmetric hydrogenation of activated imines in trifluoroethanol. The asymmetric hydrogenation of N-diphenylphosphinyl ketimines 3 with Pd(CF3CO2)/(S)-SegPhos indicated 87-99% ee, and N-tosylimines 5 could gave 88-97% ee with Pd-(CF3CO 2)/(S)-SynPhos as a catalyst. Cyclic N-sulfonylimines 7 and 11 were hydrogenated to afford the useful chiral sultam derivatives in 79-93% ee, which are important organic synthetic intermediates and structural units of agricultural and pharmaceutical agents.

A highly enantioselective, Pd-TangPhos-catalyzed hydrogenation of N-tosylimines

(Chemical Equation Presented) A catalyst system composed of Pd-(OCOCF 3)2 complexed with the electron-donating, rigid chiral diphosphane Tang-Phos gives excellent enantioselectivities (up to 99% ee) and conversions (up to > 99%) in the hydrogenation of N-tosylimines 1 (see scheme). A variety of aromatic, aliphatic, and cyclic chiral amines 2 can be prepared by this methodology.

The effect of coordination on the reaction of N-tosyl imines with diethylzinc

The effect of coordination on the reaction of N-tosyl imines and diethylzinc was studied in detail. It showed that there was strong coordination between N-tosyl imine and diethylzinc. Due to this coordination, N-tosyl imines could be reduced directly thro

New chiral ferrocenyl amidophosphine ligand for remarkable improvement of enantioselectivities in copper-catalyzed addition of diethylzinc to N-sulfonylimines

(S)-N-Ferrocenoyl-2-[(diphenylphosphino)methyl]-pyrrolidine 3 was conveniently prepared from commercially available l-proline and ferrocenecarboxylic acid. In the presence of a catalytic amount of chiral ligand 3 (4 mol %) and Cu(OTf)2 (3 mol %), the asymmetric addition of diethylzinc to N-sulfonylimines was achieved in 57-99% yield with up to 88% ee.