937717-90-3

Usage

Uses

Used in Pharmaceutical Industry:
(R_S,S)-N-(2-chloro-1-phenylethyl)-tert-butanesulfinamide is used as a chiral auxiliary for [asymmetric synthesis of pharmaceutical products] because of its ability to contribute to the production of stereochemically pure substances, which are vital for the development of effective and safe medications.
Used in Agrochemicals:
(R_S,S)-N-(2-chloro-1-phenylethyl)-tert-butanesulfinamide is used as a chiral auxiliary for [asymmetric synthesis of agrochemicals] due to its role in creating molecules with specific three-dimensional shapes, which are essential for the development of targeted and effective agrochemical products.
Used in High-Value Chemicals:
(R_S,S)-N-(2-chloro-1-phenylethyl)-tert-butanesulfinamide is used as a chiral auxiliary for [asymmetric synthesis of high-value chemicals] as it plays a significant role in the production of stereochemically pure substances, which are crucial for various applications in the chemical industry.
Used in Drug Discovery and Development:
(R_S,S)-N-(2-chloro-1-phenylethyl)-tert-butanesulfinamide is used as an important reagent for [synthesis of optically active compounds] in the field of drug discovery and development, as it aids in the creation of molecules with specific three-dimensional shapes that are essential for the development of new drugs and therapies.

Upstream product

• 1253645-10-1 (Rs)-2-methyl-N-((S)-2,2,2-trichloro-1-phenylethyl)propane-2-sulfinamide 
• 196929-85-8 (R)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 1172578-24-3 C₁₂H₁₆ClNOS 
• 532-27-4 1-chloroacetophenone 
• 937717-76-5 (R_S)-N-[2-chloro-1-phenylethylidene]-tert-butanesulfinamide 

Downstream Products

• 644963-35-9 (R_S,S)-N-(tert-butylsulfinyl)-2-phenylaziridine 

Relevant academic research and scientific papers

Stereoselective synthesis of α-(dichloromethyl)-amines, α-(chloromethyl)amines, and α-chloro-aziridines

Protocols for the stereoselective synthesis of α-(dichloromethyl) amines, α-(chloromethyl)amines, and α-chloroaziridines are presented. Diastereoselective synthesis of α-(dichloromethyl)amines was achieved based on nucleophilic dichloromethylation of aromatic N-tert-butylsulfinyl aldimines with (dichloromethyl)trimethylsilane at a low reaction temperature. Slowly warming the reaction mixture up to room temperature gave α-chloro cis-aziridines. Additionally, with Bu3SnH as the reductant, α-(dichloromethyl)amines were readily obtained from easily accessible α-(trichloromethyl)amines via mono-dechlorination. Over-reduction was successfully suppressed. Subsequent radical mono-dechlorination of the α-(dichloromethyl)amines gave the corresponding α-(chloromethyl)amines in good to excellent yields.

Asymmetric synthesis of chiral primary amines by transfer hydrogenation of N -(tert -Butanesulfinyl)ketimines

(Figure presented) The diastereoselective reduction of (R)-N-(tert- butanesulfinyl)ketimines by a ruthenium-catalyzed asymmetric transfer hydrogenation process in isopropyl alcohol, followed by desulfinylation of the nitrogen atom, is an excellent method to prepare highly enantiomerically enriched α-branched primary amines (up to >99% ee) in short reaction times (1-4 h). (1S,2R)-1-Amino-2-indanol has been shown to be a very efficient ligand to perform this transformation. Ketimines bearing either an aryl or a heteroaryl group and an alkyl group as substituents of the iminic carbon atom are very good substrates for this process. The reduction of a dialkyl ketimine could also be achieved, affording the expected amine with moderate optical purity (69% ee). Some amines which are precursors of very interesting biologically and pharmacologically active compounds have been prepared in excellent yields and enantiomeric excesses.

Asymmetric synthesis of aziridines by reduction of N-tert-butanesulfinyl α-chloro imines

(Chemical Equation Presented) Reduction of (RS)-N-tert- butanesulfinyl α-halo imines afforded chiral aziridines in good to excellent yields. Upon reduction of (RS)-N-tert-butanesulfinyl α-halo imines with NaBH4 in THF, in