66558-07-4

Upstream product

• 3789-61-5 (R)-α-(1-naphthyl)benzylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 36216-15-6 (E)-N-naphthalen-1-methylene-4-toluenesulfonamide 
• 98-80-6 phenylboronic acid 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 13922-41-3 1-Naphthylboronic acid 
• 3262-89-3 triphenylboroxine 
• 36216-15-6 4-methyl-N-(naphthalen-1-ylmethylene)benzenesulfonamide 
• 642-29-5 1-benzoylnaphthalene 
• 70-55-3 toluene-4-sulfonamide 
• 866993-20-6 (S)-4-methyl-N-(1-phenylethylidene)benzenesulfinamide 
• 100-47-0 benzonitrile 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 66558-08-5 4-Methyl-benzenesulfinic acid ((S)-naphthalen-1-yl-phenyl-methyl)-amide 

Downstream Products

• 3789-61-5 (R)-α-(1-naphthyl)benzylamine 

Relevant academic research and scientific papers

Pd(II)/(S)-t-BuPyOx-catalyzed asymmetric addition of arylboronic acids to N-sulfonyl-arylaldimines

The asymmetric version of Pd(II)/bipyridine-catalyzed nucleophilic addition of arylboronic acids to N-sulfonyl arylaldimines was developed, and excellent asymmetric induction was achieved by the use of chiral pyridinooxazoline ligand (S)-t-BuPyOx. Moistur

Heterogeneous Rh and Rh/Ag bimetallic nanoparticle catalysts immobilized on chiral polymers

The development of heterogeneous chiral catalysts has lagged far behind that of homogeneous chiral catalysts in spite of their advantages, such as environmental friendliness for a sustainable society. We describe herein novel heterogeneous chiral Rh and Rh/Ag bimetallic nanoparticle catalysts consisting of polystyrene-based polymers with chiral diene moieties. The catalysts enable high-to-excellent yields and enantioselectivities to be obtained in asymmetric 1,4-addition reactions of arylboronic acids with α,β-unsaturated carbonyl compounds such as ketones, esters, and amides, and in other asymmetric reactions. The catalysts could be readily recovered by simple filtration and reused; they could also be applied to continuous-flow synthesis. We also discuss the nature of possible reaction species based on XPS analysis.

Chiral benzene backbone-based sulfoxide-olefin ligands for highly enantioselective Rh-catalyzed addition of arylboronic acids to: N-tosylarylimines

An efficient Rh-catalyzed addition of arylboronic acids to N-tosylarylimines has been developed with chiral benzene backbone-based sulfoxide-olefin ligands, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be more effective.

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.

Rhodium-Catalyzed Asymmetric Addition of Organoboronic Acids to Aldimines Using Chiral Spiro Monophosphite-Olefin Ligands: Method Development and Mechanistic Studies

The synthesis of a novel type of chiral spiro monophosphite-olefin (SMPO) ligands based on a hexamethyl-1,1′-spirobiindane scaffold was accomplished starting from Bisphenol C. The optimal ligand could serve as an elegant chiral bidentate ligand in the Rh-catalyzed asymmetric 1,2-addition of organoboronic acids to various acyclic/cyclic aldimines, leading to chiral amines with high yields and excellent enantioselectivities. Detailed stereochemical models for enantioselective induction were elucidated through DFT calculations and postulated the origins of the higher enantioselectivity of phosphite-olefin ligands.

Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles

Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported to date for these reactions. The reusability of the catalyst was also demonstrated.

Enantioselective palladium-catalyzed arylation of N-tosylarylimines with arylboronic acids using a chiral 2,2′-bipyridine ligand

With the aid of an axially chiral 2,2′-bipyridine ligand, we have successfully developed a palladium-catalyzed method for the enantioselective arylation of N-tosylarylimines, furnishing the chiral diarylmethamines with high yields and enantioselectivities

Development of new P-chiral P,π-dihydrobenzooxaphosphole hybrid ligands for asymmetric catalysis

A new family of P-chiral P,π-hybrid ligands was prepared from the dihydrobenzooxaphosphole core. These new ligands were demonstrated to be both sterically and electronically tunable at the substituents on the phosphorus atom and the π-system of the ligand. Application of these new ligands to the catalytic asymmetric addition of boronic acids to imine electrophiles was shown to proceed with high levels of enantioinduction. (Chemical Equation Presented).

C 1-symmetric dicyclopentadienes as new chiral diene ligands for asymmetric rhodium-catalyzed arylation of N-tosylarylimines

Monosubstituted C1-symmetric dicyclopentadienes as a new class of diene ligands have been developed for asymmetric arylation of N-tosylarylimines in excellent yields (98-99%) with high enantioselectivities (90-96%). The preparation of these diene ligands relied on an efficient lipase-catalyzed resolution as the key step.

An N-linked bidentate phosphoramidite ligand (N-Me-BIPAM) for rhodium-catalyzed asymmetric addition of arylboronic acids to N-sulfonylarylaldimines

A chiral N-linked C2-symmetric bidentate phosphoramidite (N-Me-BIPAM) was newly developed for the rhodium-catalyzed enantioselective addition of arylboronic acids to N-sulfonylimines. This ligand achieved high enantioselectivities in a range of