607729-50-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(S)-2,4,6-TRIMETHYLBENZENESULFINAMIDE serves as an essential intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure contributes to the development of new and effective compounds for medical and agricultural applications.
Used as a Chiral Auxiliary in Organic Synthesis:
In the field of organic synthesis, (S)-2,4,6-TRIMETHYLBENZENESULFINAMIDE is utilized as a chiral auxiliary, particularly for the construction of chiral compounds. Its ability to induce chirality aids in the creation of enantiomerically pure products, which is crucial for the development of pharmaceuticals with specific biological activities.
Used in Catalytic Asymmetric Reactions:
(S)-2,4,6-TRIMETHYLBENZENESULFINAMIDE has been studied for its potential use in catalytic asymmetric reactions. Its unique properties allow it to act as a catalyst, facilitating the formation of enantioselective products, which is vital for the synthesis of biologically active compounds with desired stereochemistry.

Upstream product

• 1351958-44-5 quinine (Rs)-2,4,6-trimethylbenzenesulfinate 
• 2633-66-1 2-mesitylmagnesium bromide 
• 847980-51-2 N-chloroacetyl-2,4,6-trimethylbenzenesulfinamide 
• 137280-49-0 2,4,6-trimethylbenzenesulphinamide 
• 847980-61-4 (S)-N-chloroacetyl-2,4,6-trimethylbenzenesulfinamide 

Downstream Products

• 855475-24-0 (S)-(+)-N-(benzylidene)-2,4,6-trimethylbenzenesulfinamide 
• 607729-55-5 diethyl (S_S,2S,3R)-(+)-N-(mesitylsulfinyl)-3-phenylaziridine-2-phosphonate 
• 607729-56-6 diethyl (S_S,2S,3R)-(+)-N-(mesitylsulfinyl)-3-(p-methoxyphenyl)aziridine-2-phosphonate 
• 1157952-61-8 (+)-(S)-2,4,6-trimethyl-N-[(1E)-2-methylpropylidene]benzenesulfinamide 

Relevant academic research and scientific papers

Asymmetric synthesis of sulfinamides using (-)-quinine as chiral auxiliary

A process has been designed and demonstrated for the asymmetric synthesis of sulfinamides using quinine as auxiliary. A variety of chiral sulfinamides including N-alkyl sulfinamides with diverse structure were prepared in good yields and excellent enantioselectivity starting from easily available and inexpensive reagents. The auxiliary quinine could be recovered and recycled.

One-pot synthesis of chiral nonracemic amines

One-pot five-component reactions of oxathiazolidine-S-oxides with mesitylmagnesium bromide, lithium bis(trimethylsilyl)amide, aldehydes and Grignard reagents afford chiral nonracemic amines or sulfinamides in good yields and high stereoselectivities.

Subtilisin-catalyzed resolution of N-acyl arylsulfinamides

We report the first biocatalytic route to sulfinamides (R-S(O)-NH 2), whose sulfur stereocenter makes them important chiral auxiliaries for the asymmetric synthesis of amines. Subtilisin E did not catalyze hydrolysis of N-acetyl or N-butanoyl arylsulfinamides, but did catalyze a highly enantioselective (E > 150 favoring the (R)-enantiomer) hydrolysis of N-chloroacetyl and N-dihydrocinnamoyl arylsulfinamides. Gramscale resolutions using subtilisin E overexpressed in Bacillus subtilis yielded, after recrystallization, three synthetically useful auxiliaries: (R)-p- toluenesulfinamide (42% yield, 95% ee), (R)-p-chlorobenzenesulfinamide (30% yield, 97% ee), and (R)-2,4,6-trimethylbenzenesulfinamide (30% yield, 99% ee). Molecular modeling suggests that the N-chloroacetyl and N-dihydrocinnamoyl groups mimic a phenylalanine moiety and thus bind the sulfinamide to the active site. Molecular modeling further suggests that enantioselectivity stems from a favorable hydrophobic interaction between the aryl group of the fast-reacting (R)-arylsulfinamide and the S1′ leaving group pocket in subtilisin E.

Practical and highly stereoselective technology for preparation of enantiopure sulfoxides and sulfinamides utilizing activated and functionally differentiated N-sulfonyl-1,2,3-oxathiazolidine-2-oxide derivatives

A simple, general, and practical technology to prepare enantiopure 1,2,3-oxathiazolidine-2-oxide derivatives using chiral aryl N-sulfonyl aminoalcohol derivatives and thionyl chloride is reported. The versatility of these novel chiral building blocks (MIOO and TMPOO), was exemplified by the expedient production of a variety of unique chiral sulfoxides and valuable chiral sulfinamides in excellent yields and enantiopurities.

Application of P,N-Sulfinyl Imine Ligands to Iridium-Catalyzed Asymmetric Hydrogenation of Olefins

The utility of a novel class of P,N-ligands incorporating a chiral sulfinyl imine moiety is demonstrated in the iridium-catalyzed hydrogenation of both functionalized and unfunctionalized olefins, in which enantioselectivities of up to 94% are achieved. T

Improved asymmetric synthesis of aziridine 2-phosphonates using (S)-(+)-2,4,6-trimethylphenylsulfinamide

The aza-Darzens reaction of lithium diethyl iodomethylphosphonate with enantiopure N-(2,4,6-trimethylphenylsulfinyl)imines affords a single diastereomeric N-sulfinylaziridine 2-phosphonate which, on treatment with MeMgBr, gives the corresponding NH-azirid