153277-49-7

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(+)-P-TOLUENESULFINAMIDE N-BENZYLIDENE is used as a chiral auxiliary for the enantioselective synthesis of pharmaceutical compounds. Its role in the Sharpless asymmetric dihydroxylation reaction allows for the production of enantiomerically pure compounds, which is crucial for the development of effective and safe medications.
Used in Fine Chemical Industry:
In the fine chemical industry, (S)-(+)-P-TOLUENESULFINAMIDE N-BENZYLIDENE is utilized as a key reagent in the synthesis of chiral fine chemicals. Its ability to assist in the enantioselective synthesis of various organic molecules contributes to the creation of high-quality specialty chemicals with specific applications.
Used in Organic Synthesis Research:
(S)-(+)-P-TOLUENESULFINAMIDE N-BENZYLIDENE is employed as a chiral auxiliary in academic and research settings, where it aids chemists in the development of novel synthetic methods and the exploration of asymmetric synthesis. Its use in research contributes to the advancement of organic chemistry and the discovery of new compounds with potential applications.

Upstream product

• 100-52-7 benzaldehyde 
• 188447-91-8 (S)-p-toluenesulfinimide 
• 6873-55-8 p-tolylsulfinyl amide 
• 100-51-6 benzyl alcohol 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 

Downstream Products

• 852332-86-6 [1R,2S,(S)S]-N-{1-phenyl-2-[(S)-2-(p-toluenesulfinyl)phenyl]-2-(methylthio)ethyl}-p-toluenesulfinamide 
• 503819-30-5 [1S,(S)S]-N-{1-phenyl-2[(S)-2-(p-toluensulfinyl)phenyl]ethyl}-p-toluenesulfinamide 
• 503819-32-7 [1S,2S,(S)S]-N-{1-phenyl-2-[(S)-2-(p-toluenesulfinyl)phenyl]propyl}-p-toluenesulfinamide 
• 868056-35-3 (1S,(S)S)-N-(p-tolylsulfinyl)-2-nitro-1-phenylethanamine 
• 1073146-94-7 (2R,3R)-4-methylene-2-phenyl-1-((S)-toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diethylamide 
• 1073146-88-9 (2R,3R)-4-methylene-2-phenyl-1-((S)-toluene-4-sulfinyl)-pyrrolidine-3-carbothioic acid S-tert-butyl ester 
• 1073146-89-0 (2R,3R)-4-methylene-2-phenyl-1-((S)-toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid bis-(4-methoxy-phenyl)-amide 
• 1073146-91-4 (2R,3R)-4-methylene-2-phenyl-1-((S)-toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid methyl-phenyl-amide 
• 1073146-92-5 (2R,3R)-4-methylene-2-phenyl-1-((S)-toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid allyl-phenyl-amide 
• 1073146-93-6 (2R,3R)-4-methylene-2-phenyl-1-((S)-toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diallylamide 

Relevant academic research and scientific papers

1,8-Diazabicyclo[5.4.0]undec-7-ene-mediated formation of N-sulfinyl imines

A facile and efficient method was developed for the preparation of a variety of aryl, heteroaryl, and alkyl N-sulfinyl imines using 1,8-diazabicyclo[5.4.0]undec-7-ene. In addition to tert-butanesulfinamide, the condensation is also effective with p-toluenesulfinamide. The reaction was performed at room temperature and produces the corresponding N-sulfinyl imines in excellent yields in the absence of acids, metals, and additives. This methodology is also useful for the preparation of N-sulfinyl imines on gram scale. A one-pot synthesis was developed using aryl and heteroaryl alcohols with both tert-butanesulfinamide and p-toluenesulfinamide at room temperature, resulting in the corresponding N-sulfinyl imines with good yields.

Synthesis of amino-diamondoid pharmacophores: Via photocatalytic C-H aminoalkylation

We report a direct C-H aminoalkylation reaction using two light-activated H-atom transfer catalyst systems that enable the introduction of protected amines to native adamantane scaffolds with C-C bond formation. The scope of adamantane and imine reaction partners is broad and deprotection provides versatile amine and amino acid building blocks. Using readily available chiral imines, the enantioselective synthesis of the saxagliptin core and rimantadine derivatives is also described.

Stereocontrolled Addition of Scrambling ortho-Sulfinyl Carbanions: Easy Access to Homopropargylamines and α-Allenylamines

An unprecedented behavior of ortho-sulfinylpropargyl carbanions in the presence of optically active sulfinylimines affords two different families of compounds: This peculiar chemodivergency is importantly affected by the nature of the employed base, and a

Stereoselective synthesis of β-amino acid derivatives by asymmetric mannich reaction in flow

A continuous flow synthesis of β-amino acid derivatives has been demonstrated using an asymmetric Mannich reaction. An enolate of tert-butyl acetate was successfully prepared in 10s at room temperature in a flow reactor, and the desired β-amino acid derivatives were stereoselectively obtained within a short residence time (40 s) in moderate-to-good yields. Sequential Nalkylation of the Mannich product in the flow reactor was also achieved in the presence of DMPU that provided N-alkylated β-amino acid derivatives in good yields.

Double asymmetric induction in the synthesis of enantiomeric α-aminophosphonic acids mediated by sulfinimines

A double asymmetric induction in the synthesis of α-aminophosphonic acids is described. It involves the nucleophilic addition of anions of enantiomeric dimenthyl phosphites to both (+)-(S)- and (-)-(R)-enantiomers of N-(p-tolylsulfinyl)benzaldimine and subsequent acidic hydrolysis of the adducts formed. The match and mismatch effects were observed.

A general aminocatalytic method for the synthesis of aldimines

A general and efficient biomimetic method for the synthesis of aldimines from aldehydes and compounds bearing the NH2 group in the presence of pyrrolidine as a catalyst has been developed. These organocatalytic reactions, based on the application of the concept of nucleophilic catalysis, proceed with outstanding yields in the absence of acids and metals under simple conditions and minimum experimental manipulation. The method has been mainly applied to the synthesis of N-sulfinyl and N-sulfonyl imines, but its general validity has been proven with the preparation of representative N-phosphinoyl, N-alkyl, and N-aryl imines. These unprecedented reactions, which presumably occur via iminium activation without requiring acidic conditions, are an interesting and competitive alternative to the classical methods for preparing aldimines.

Microwave-assisted solvent-free synthesis of enantiomerically pure N-(tert-butylsulfinyl)imines

A simple, environmentally friendly, and very efficient procedure for the synthesis of optically pure N-(tert-butylsulfinyl)imines has been developed with microwave-promoted condensation of aldehydes and ketones using (R)-2-methylpropane-2-sulfinamide in the presence of Ti(OEt)4, under solvent-free conditions. This procedure allows for the preparation of a variety of sulfinyl aldimines with excellent yields and purities in only 10 min, making any further purification of the imines unnecessary. Several sulfinyl ketimines have also been prepared in good yields by extension of the reaction times to 1 h. This methodology has proved to be equally efficient for the synthesis of aromatic, heteroaromatic, and aliphatic N-(tert-butylsulfinyl)imines. Conventional heating has also been shown to be useful to promote these reactions, especially for the synthesis of aldimines.

Asymmetric synthesis of ethoxydienamines in superbasic medium mediated by chiral sulfinyl group

The direct addition of metalated alkoxydiene 2, obtained from α,β-unsaturated acetal 1 through a LIC-KORpromoted conjugated elimination reaction, to enantiopure sulfinimines 3 (both R and S N-sulfinyl imines) afforded Nsulfinyl alkoxydienyl amines 4 with

Asymmetric organocatalytic allylic substitution of Morita-Baylis-Hillman carbonates with allylamines for the synthesis of 2,5-dihydropyrroles

(Figure presented) The asymmetric allylic substitution reaction of MBH carbonates with allylamines has been developed, which affords N-allyl-β-amino-α-methylene esters in high yields and enantioselectivities. After a subsequent ring-closure metathesis of

An efficient method for the synthesis of nitropiperidones

(Chemical Equation Presented) A three step efficient strategy for the synthesis of substituted 5-nitropiperidones in high de, employing Michael addition of N-p-tolylsulfinyl β-nitroamines to α,β-unsaturated esters, hydrolysis of the sulfinyl group, and cyclization of the resulting free amines, has been developed. A very simple experimental procedure involving mild conditions and only one chromatographic purification are the main features of the process.