592507-77-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-(+)-2,4,6-triisopropylphenylsulfinamide is used as a chiral auxiliary in the synthesis of pharmaceuticals. Its role is crucial in controlling the stereochemistry of the products, ensuring the production of the desired enantiomers with high purity and selectivity.
Used in Agrochemical Production:
In the agrochemical industry, (R)-(+)-2,4,6-triisopropylphenylsulfinamide is employed as a chiral auxiliary for the synthesis of chiral pesticides and other agrochemicals. Its use helps in controlling the stereochemistry of the final products, which is essential for their biological activity and selectivity.
Used in Chiral Ligand Production for Catalysis:
(R)-(+)-2,4,6-triisopropylphenylsulfinamide is also utilized in the production of chiral ligands for catalysis. These ligands are vital in asymmetric catalysis, a process that allows for the selective synthesis of enantiomerically pure compounds, which are often required for their specific biological activities.
Used in Asymmetric Synthesis Reactions:
As a chiral auxiliary, (R)-(+)-2,4,6-triisopropylphenylsulfinamide is widely used in asymmetric synthesis reactions. It aids in controlling the stereochemistry of the products, leading to the formation of the desired enantiomers with high enantioselectivity and yield. This is particularly important in the synthesis of complex organic molecules with multiple chiral centers.

Upstream product

• 1351958-45-6 quinine (Rs)-2,4,6-triisopropylbenzenesulfinate 
• 1310105-60-2 C₃₂H₄₃NO₄S₂ 
• 21524-34-5 2,4,6-triisopropyl-1-bromobenzene 

Downstream Products

• 1374824-04-0 (R)-2,4,6-triisopropyl-N-((2-methyl-2-(4-pivaloylpiperazin-1-yl)propyl)carbamoyl)benzenesulfinamide 
• 1374824-05-1 (R)-benzyl 4-(2-methyl-1-(3-((2,4,6-triisopropylphenyl)sulfinyl)ureido)propan-2-yl)piperazine-1-carboxylate 
• 1374824-06-2 (R)-2,4,6-triisopropyl-N-((2-methyl-2-(4-tosylpiperazin-1-yl)propyl)carbamoyl)benzenesulfinamide 
• 1374824-07-3 (R)-2,4,6-triisopropyl-N-((2-methyl-2-(4-methylpiperazin-1-yl)propyl)carbamoyl)benzenesulfinamide 
• 1374823-93-4 C₃₀H₃₉N₃O₂S 
• 1374823-91-2 C₁₈H₃₁N₃O₂S 
• 1374823-92-3 C₂₀H₃₅N₃O₂S 
• 1374823-94-5 (R)-2,4,6-triisopropyl-N-((2-(piperidin-1-yl)ethyl)carbamoyl)benzenesulfinamide 
• 1374823-95-6 (R)-2,4,6-triisopropyl-N-((2-methyl-2-(piperidin-1-yl)propyl)carbamoyl)benzenesulfinamide 
• 1374824-00-6 (R)-2,4,6-triisopropyl-N-((2-methyl-2-(pyrrolidin-1-yl)propyl)carbamoyl)benzenesulfinamide 
• 1374824-01-7 (R)-N-((2-(azepan-1-yl)-2-methylpropyl)carbamoyl)-2,4,6-triisopropylbenzenesulfinamide 
• 1429442-69-2 (R)-N-((S)-4-(dimethylamino)-3,3-dimethyl-1-morpholino-1-oxobutan-2-yl)-2,4,6-triisopropylbenzenesulfinamide 
• 1429442-63-6 (R)-N-(3-(dimethylamino)-2,2-dimethylpropylidene)-2,4,6-triisopropylbenzenesulfinamide 

Relevant academic research and scientific papers

Effective tuning of the arene and alkanesulfinamides for highly enantioselective synthesis of (S)-4-chlorophenylphenylmethylamine, a key intermediate for antihistamic (S)-cetirizine

High diastereoselectivity (>94%) has been achieved in the phenylMgBr addition process to chlorophenyl aldimine derived from the new and sterically hindered triisopropylbenzene sulfinamide (TIPBSA) in the synthesis of a key intermediate of (S)-Cetirizine. Surprisingly, under the same reaction conditions, toluenesulfinamide derived chlorophenyl aldimine provided only 10% ee.

Design and synthesis of chiral oxathiozinone scaffolds: Efficient synthesis of hindered enantiopure sulfinamides and sulfinyl ketimines

Is that S-O? The title scaffolds have a highly active and properly differentiated S-O bond for the efficient synthesis of enantiopure sulfinamides. The method is practical, green, and has the potential to provide an economical commercial process for the synthesis of bulky sulfinamides. Copyright

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.

Enantioselective synthesis of diverse sulfinamides and sulfinylferrocenes from phenylglycine-derived chiral sulfinyl transfer agent

A new chiral sulfinyl transfer auxiliary derived from readily available phenylglycine was developed. This auxiliary is utilized to synthesize a diverse array of alkyl- and arylsulfinamides and sulfinylferrocenes in high yields and excellent ee's. The desired products are produced in a one-pot sequence from the oxathiazolidine 2-oxide by two sequential nucleophilic additions that proceed in a stereospecific manner.

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