72938-93-3

Upstream product

• 3886-70-2 (R)-1-(1-Naphthyl)ethylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 941-55-9 4-toluenesulfonyl azide 
• 1127-76-0 1-ethylnapthelene 
• 941-98-0 1'-naphthacetophenone 
• 70-55-3 toluene-4-sulfonamide 
• 182949-56-0 C₁₉H₁₇NO₂S 
• 823-96-1 Trimethylboroxine 
• 36216-15-6 4-methyl-N-(naphthalen-1-ylmethylene)benzenesulfonamide 

Downstream Products

• 72953-41-4 N-(2,4-Dinitro-phenylsulfanyl)-4-methyl-N-((R)-1-naphthalen-1-yl-ethyl)-benzenesulfonamide 
• 72938-98-8 N-(4-Chloro-2-methyl-phenylsulfanyl)-4-methyl-N-((R)-1-naphthalen-1-yl-ethyl)-benzenesulfonamide 
• 72939-01-6 4-Methyl-N-((R)-1-naphthalen-1-yl-ethyl)-N-(2-nitro-phenylsulfanyl)-benzenesulfonamide 
• 72938-96-6 4-Methyl-N-((R)-1-naphthalen-1-yl-ethyl)-N-trichloromethylsulfanyl-benzenesulfonamide 

Relevant academic research and scientific papers

Nickel-Catalyzed Asymmetric Transfer Hydrogenation and α-Selective Deuteration of N-Sulfonyl Imines with Alcohols: Access to α-Deuterated Chiral Amines

A nickel-catalyzed enantioselective transfer hydrogenation and deuteration of N-sulfonyl imines was developed. Excellent α-selectivity and high deuterium content were achieved by using inexpensive 2-propanol-d8 as a deuterium source. As a highlight, no deuteration of β-C-H and the remote C-H of N-sulfonyl amines occurred, which is hard to achieve using other imines or by hydrogen isotope exchange with D2O. Mechanism studies indicated a stepwise pathway through the [Ni-D] intermediate.

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.

Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme

C-H bonds are ubiquitous structural units of organic molecules. Although these bonds are generally considered to be chemically inert, the recent emergence of methods for C-H functionalization promises to transform the way synthetic chemistry is performed. The intermolecular amination of C-H bonds represents a particularly desirable and challenging transformation for which no efficient, highly selective, and renewable catalysts exist. Here we report the directed evolution of an iron-containing enzymatic catalyst - based on a cytochrome P450 monooxygenase - for the highly enantioselective intermolecular amination of benzylic C-H bonds. The biocatalyst is capable of up to 1,300 turnovers, exhibits excellent enantioselectivities, and provides access to valuable benzylic amines. Iron complexes are generally poor catalysts for C-H amination: in this catalyst, the enzyme's protein framework confers activity on an otherwise unreactive iron-haem cofactor.

Rhodium/chiral diene-catalyzed asymmetric methylation of N-sulfonylarylimines with trimethylboroxine

A hydroxorhodium complex coordinated with a chiral diene ligand catalyzed the asymmetric addition of trimethylboroxine to N-sulfonylarylimines to give high yields of chiral 1-aryl-1-ethylamines with high enantioselectivity.

Chiroptical Properties of Sulfenamides

The ORD (and in some cases CD) spectra are presented for 11 sulfenamides of the structure R'SN(SO2Ar)CH(CH3)R (R'=CCl3, 4-chloro-2-methylphenyl, 2-nitrophenyl, 2,4-dinitrophenyl; R=phenyl, 1-naphthyl, benzyl; Ar=p-tolyl).A number of the spectra exhibit intense Cotton effects characteristic of inherently dissymmetric chromophores near 200 nm.The configuration at the asymmetric carbon atom seems to be related to the sign of the long-wavelength transition (near 350 nm) in the 2,4-dinitrobenzenesulfenamides.This is ascribed to an equilibrium asymmetric induction from the asymmetric center into the sulfenamide chiral axis whose configuration is reflected by the sign of this Cotton effect.It is suggested that examination of such derivatives may provide a useful method for determination of the absolute configuration of amines.