62596-64-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-(+)-2-Benzyl-1-(p-tolylsulfonyl)aziridine is used as a key intermediate for the synthesis of substituted octahydroindoles, which are important structural motifs in various bioactive compounds and pharmaceutical agents. Its chiral nature ensures that the desired enantioselectivity is achieved during the synthesis process.
Used in Organic Chemistry:
In the preparation of ortho-bromo phenethylamine products, (S)-(+)-2-benzyl-1-(p-tolylsulfonyl)aziridine is used as a starting material. These ortho-bromo phenethylamine products are further utilized in the synthesis of chiral 2-substituted indolines, which are valuable scaffolds in the development of new pharmaceuticals and agrochemicals.
Used in Medicinal Chemistry:
(S)-(+)-2-Benzyl-1-(p-tolylsulfonyl)aziridine is employed in the synthesis of β-aryltelluroamines, which are potent carbonic anhydrase inhibitors. These inhibitors have potential applications in the treatment of various diseases, such as glaucoma, epilepsy, and altitude sickness, by modulating the activity of carbonic anhydrase enzymes.
Overall, (S)-(+)-2-benzyl-1-(p-tolylsulfonyl)aziridine is a valuable synthetic building block with applications in the pharmaceutical, organic chemistry, and medicinal chemistry fields, contributing to the development of new drugs and chemical compounds.

InChI:InChI=1/C16H17NO2S/c1-13-7-9-16(10-8-13)20(18,19)17-12-15(17)11-14-5-3-2-4-6-14/h2-10,15H,11-12H2,1H3/t15-,17?/m0/s1

Upstream product

• 82495-70-3 (2S)-2-p-toluenesulfonamido-3-phenylpropanol 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 51220-86-1 N-(p-toluenesulfonyl)-L-phenylalanine methyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 74555-64-9 C₂₃H₂₅NO₅S₂ 
• 63-91-2 L-phenylalanine 
• 3182-95-4 L-Phenylalaninol 
• 13505-32-3 N-tosyl-(S)-phenylalanine 
• 203871-38-9 (S)-2-(diphenylphosphinamido)-3-phenylpropan-1-ol 

Downstream Products

• 74555-65-0 2,2-bis(ethylthio)-4S-(p-toluenesulphonamido)-5-phenylpentanoic acid 
• 132161-97-8 (S)-N-(1-Cyano-3-phenylpropan-2-yl)-4-methylbenzenesulfonamide 
• 134746-09-1 (S)-1-[(S)-3-Phenyl-2-(toluene-4-sulfonylamino)-propyl]-piperidine-2-carboxylic acid 
• 154047-35-5 (S)-1-(1,3-dithian-2-yl)-2-(4-methylbenzenesulfonamido)-3-phenylpropane 
• 154047-37-7 (S)-1-(2-methyl-1,3-dithian-2-yl)-2-(4-methylbenzenesulfonamido)-3-phenylpropane 
• 154047-41-3 (S)-1-(2-trimethylsilyl-1,3-dithian-2-yl)-2-(4-methylbenzenesulfonamido)-3-phenylpropane 
• 203452-43-1 (2S,4S)-2-Benzyl-6-methyl-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine 
• 203207-78-7 N-[(S)-1-Benzyl-5,5-dimethoxy-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide 
• 73058-30-7 (2S)-2-benzylazacyclopropane 
• 2038-57-5 3-Phenylpropan-1-amine 
• 5435-02-9 4-methyl-N-(3-phenylpropyl)benzenesulfonamide 
• 85612-60-8 (2S)-3-phenylpropane-1,2-diamine 
• 5848-57-7 4-methyl-N-[(2E)-3-phenylprop-2-en-1-yl]benzene-1-sulfonamide 
• 229974-87-2 (2S,4S)-N-<4-isocyano-4-(4-methoxyphenyl)-1-phenyl-2-butyl>-p-toluenesulfonamide 

Relevant academic research and scientific papers

Ni-Catalyzed Carboxylation of Aziridines en Route to β-Amino Acids

A Ni-catalyzed reductive carboxylation of N-substituted aziridines with CO2 at atmospheric pressure is disclosed. The protocol is characterized by its mild conditions, experimental ease, and exquisite chemo- and regioselectivity pattern, thus unlocking a new catalytic blueprint to access β-amino acids, important building blocks with considerable potential as peptidomimetics.

Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1: H -azepines

Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K2CO3 gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.

Carbon Isotope Labeling Strategy for β-Amino Acid Derivatives via Carbonylation of Azanickellacycles

A series of 4-membered azametallacycles have been prepared by the oxidative addition of Ni(0) with aziridines. Stoichiometric 13C-labeled carbon monoxide could be efficiently incorporated via Ni-C bond insertion to generate air stable and isola

Cu-Catalyzed [3 + 3] Cycloaddition of Isocyanoacetates with Aziridines and Stereoselective Access to α,γ-Diamino Acids

We report herein an efficient Cu-catalyzed formal [3 + 3] cycloaddition of isocyanoacetates with readily available aziridines of different substitution patterns, which provides a practical access to valuable 1,4,5,6-tetrahydropyrimidine derivatives. In pa

Synthesis of tubuphenylalanine and epi-tubuphenylalanine via regioselective aziridine ring opening with carbon nucleophiles followed by hydroboration-oxidation of 1,1-substituted amino alkenes

An efficient synthesis of N-Boc-tubuphenylalanine benzyl ester (N-Boc-Tup-OBn, 1a) and N-Boc-epi-tubuphenylalanine benzyl ester (N-Boc-epi-Tup-OBn, 1b) is reported herein. Regioselective aziridine 4 ring opening with carbon nucleophiles followed by hydrob

Enantiodivergent Synthesis of (+)- and (?)-Pyrrolidine 197B: Synthesis of trans-2,5-Disubstituted Pyrrolidines by Intramolecular Hydroamination

A highly efficient, diastereoselective, iron(III)-catalyzed intramolecular hydroamination/cyclization reaction involving α-substituted amino alkenes is described. Thus, enantiopure trans-2,5-disubstituted pyrrolidines and trans-5-substituted proline derivatives were synthesized by means of a combination of enantiopure starting materials, easily available from l-α-amino acids, with sustainable metal catalysts such as iron(III) salts. The scope of this methodology is highlighted in an enantiodivergent approach to the synthesis of both (+)- and (?)-pyrrolidine 197B alkaloids from l-glutamic acid. In addition, a computational study was carried out to gain insight into the complete diastereoselectivity of the transformation.

An efficient synthetic approach for N-C bond formation from (S)-amino acids: An easy access to cis-2,5-disubstituted chiral piperazines

An efficient synthetic strategy is described for the construction of amino acids derived enantiomerically pure cis-2,5-disubstituted chiral piperazines. Cu-catalyzed spontaneous regioselective ring opening and ring closing of non-activated N-tosyl aziridines as well as Pd-mediated N-C bond formation from N-tosyl halogenated amino-derivatives are the key steps for accessing disubstituted piperazines.

Stereodefined N,O-acetals: Pd-catalyzed synthesis from homopropargylic amines and utility in the flexible synthesis of 2,6-substituted piperidines

We developed a conceptually new synthetic strategy which exploits the stereochemical information of labile acyclic N,O-acetals. The key to this strategy, chemo- and stereoselective synthesis of N,O-acetals, was achieved by the Pd-catalyzed addition of sulfonyl-protected homopropargylic amines to alkoxyallene. The N,O-acetals generated in this way were combined with Au-catalyzed cycloisomerization to give an access to 2,6-disubstituted piperidines with stereochemical flexibility.

One-pot and microwave-assisted synthesis of N-sulfonylaziridines

A novel and efficient microwave-assisted one-step reaction was developed to synthesize chiral N-sulfonylaziridines by the reaction of different chiral amino alcohols and sulfonic chlorides. The newly developed microwave synthetic method has the advantage of reducing the reaction time from 24 to 0.5 h with improved yields (84-93%) and minimizing by-products.

Regioselective ring-opening of amino acid-derived chiral aziridines: An easy access to cis-2,5-disubstituted chiral piperazines

An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF3·OEt2)-mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. The pied piperazines: A four-step efficient synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino acid-based aziridines is described. The key reaction steps are the highly regioselective BF3·OEt2 mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochlorides, followed by a Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. Copyright