63160-12-3

Usage

Uses

Used in Organic Synthesis:
3-Phenyl-2-tosyl-1,2-oxaziridine is used as an oxidation reagent for the selective and efficient oxidation of a variety of functional groups, including alkenes, sulfides, and amines. Its mild reaction conditions and broad applicability make it a valuable tool in the field of synthetic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Phenyl-2-tosyl-1,2-oxaziridine is used as a key intermediate in the synthesis of complex organic molecules and drug candidates. Its ability to selectively oxidize functional groups contributes to the development of novel and effective pharmaceutical compounds.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 3-Phenyl-2-tosyl-1,2-oxaziridine serves as an important building block for the preparation of complex organic molecules used in the development of agrochemicals, such as pesticides and herbicides. Its selective oxidation properties facilitate the synthesis of new and improved agrochemical products.

Upstream product

• 57272-54-5 N-benzylidene-S-p-tolylthiohydroxylamine 
• 774-48-1 (diethoxymethyl)benzene 
• 100-52-7 benzaldehyde 
• 70-55-3 toluene-4-sulfonamide 
• 51608-60-7 phenyl N-tosyl imine 
• 52962-78-4 4-methyl-N-(phenyl(phenylsulfonyl)methyl)benzenesulfonamide 
• 22955-77-7 methyl 1-indanone-2-carboxylate 
• 63160-12-3 2-[(4-methylphenyl)sulfonyl]-3-phenyl-oxaziridine 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 127-65-1 chloroamine-T 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 327040-08-4 (E)-N-benzyliden-4-methylbenzenesulfinamide 
• 672-78-6 methyl p-toluene sulfinate 
• 6873-55-8 p-tolylsulfinyl amide 

Downstream Products

• 63160-12-3 (S)-3-phenyl-2-tosyloxaziridine 
• 6971-74-0 N-benzoyl-p-toluenesulfonamide 
• 165523-69-3 (3R)-3-phenyl-2-tosyl-1,2-oxaziridine 
• 923569-32-8 (R)-adamantan-1-yl 2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 923569-21-5 (S)-adamantan-1-yl 2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 1263144-86-0 (R)-isopropyl 2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 1261666-40-3 (R)-tert-butyl 2-hydroxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 1132667-67-4 diethyl 3-phenyl-1-tosylaziridine-2,2-dicarboxylate 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Lewis acids promoted 3 + 2 cycloaddition of oxaziridines and cyclic allylic alcohols through carbonyl imine intermediates

Syntheses of isoxazolidines through the carbonyl imine intermediates are currently limited to monosubstituted olefin substrates. Herein, we reported syntheses of novel bicyclic isoxazolidine-containing compounds through 1,3-dipolar cycloaddition reactions

Oxaziridinium compound (by machine translation)

Various applications such as various reaction using compound [a] oxidant oxaziridines, safe and simple, while eliminating as much as possible intrusion of impurities which can be efficiently manufactured oxaziridinium compound production method. The follo

Novel chiral thiourea organocatalysts for the catalytic asymmetric oxaziridination

Catalytic enantioselective oxaziridination is one of the challenging reactions in the oxidation of organic molecules. In this article, a series of novel chiral thiourea moleculars were synthesized from natural cinchona alkaloids and primary amines. By usi

Ring Expansion of Donor-Acceptor Cyclopropane via Substituent Controlled Selective N-Transfer of Oxaziridine: Synthetic and Mechanistic Insights

A distinctive N-substituent controlled electrophilic N-transfer of oxaziridines with donor-acceptor cyclopropanes in the presence of MgI2 is reported. Contrary to earlier reports, the oxaziridine having bulkier N-substituents can also give N-transferred product instead of the O-transferred one. Interestingly, the oxaziridines having α-H containing N-substituents lead to the pyrrolidine derivatives through [3 + 2] cycloaddition. A mechanistic reasoning for this divergent reactivity is depicted by density functional theory calculations and validated through energy decomposition analysis.

Hydrogen peroxide/dimethyl carbonate: A green system for epoxidation of: N -alkylimines and N -sulfonylimines. One-pot synthesis of N -alkyloxaziridines from N -alkylamines and (hetero)aromatic aldehydes

A green method for epoxidation of imines using an environmentally benign oxidant system, H2O2/dimethyl carbonate, was developed. N-Alkyloxaziridines were prepared in high yields from N-alkylamines and (hetero)aromatic aldehydes in one-pot fashion, whereas N-sulfonyloxaziridines have been prepared by using the same oxidant system and 5 mol% of Zn(OAc)2·2H2O as catalyst.

Kinetic Resolution of Oxaziridines via Chiral Bifunctional Guanidine-Catalyzed Enantioselective α-Hydroxylation of β-Keto Esters

An efficient kinetic resolution of racemic oxaziridines has been realized via catalytic asymmetric α-hydroxylation of available β-keto esters. In the presence of a chiral bifunctional guanidine catalyst, a variety of optically active oxaziridines and chir

Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines

A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high d.r., yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.

Iron-catalyzed kinetic resolution of N-sulfonyl oxaziridines

We have developed a highly selective kinetic resolution of N-sulfonyl oxaziridines. This reaction utilizes an inexpensive and easily synthesized iron bis(oxazoline) catalyst to promote the efficient rearrangement of oxaziridines to the corresponding N-sulfonyl imides; no sacrificial reagents are required to effect this resolution. This process is readily translated to gram scale, which provides a practical method for the preparation of structurally diverse, enantiopure N-sulfonyl oxaziridines for use as reagents in organic synthesis.

Iron(II)-catalyzed amidation of aldehydes with iminoiodinanes at room temperature and under microwave-assisted conditions

A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C-H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)4Cl2] generated in situ from reaction of FeCl 2 with pyridine.