1313223-40-3

Upstream product

• 917-54-4 methyllithium 
• 160955-96-4 N-[1-(3-Methoxy-phenyl)-meth-(E)-ylidene]-4-methyl-benzenesulfonamide 
• 626-20-0 3-methoxystyrene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 25108-57-0 3-(1-methylethenyl)anisole 
• 127-65-1 chloroamine-T 
• 7080-50-4 chloramine T trihydrate 
• 70-55-3 toluene-4-sulfonamide 
• 941-55-9 4-toluenesulfonyl azide 

Downstream Products

• 1401247-06-0 C₂₃H₂₉NO₇S 
• 1401247-15-1 C₂₃H₂₉NO₇S 
• 1419175-30-6 C₂₃H₂₂N₂O₇S 
• 1419175-31-7 C₂₃H₂₂N₂O₇S 
• 1313223-16-3 4-(3-methoxyphenyl)-2-methyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-imidazole 

Relevant academic research and scientific papers

Synthesis of γ-Lactams by Formal Cycloadditions with Ketenes

The synthesis of γ-lactams is reported by a formal (3+2) cycloaddition between readily available ketenes and aziridines or a one-pot formal (2+1+2) cycloaddition using imines as aziridine precursors. The method is practical, is scalable, and affords high yields. It also offers a high level of regio- and diastereoselectivity on a wide range of substrates as well as a high stereoselectivity in the case of enantiopure aziridines.

Merging Photoredox/Nickel Catalysis for Cross-Electrophile Coupling of Aziridines with Pyridin-1-ium Salts via Dearomatization

Merging photoredox/nickel catalysis enabling the cross-electrophile coupling of aziridines with pyridin-1-ium salts involving dearomatization for the synthesis of β-(1,4-dihydropyridin-4-yl)-ethylamines, especially including bioactive motif-based analogue

Lewis Acid Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic N-Sulfonylaziridines

The first Lewis acid catalyzed stereoconvergent transformation of racemic 2-(hetero)aryl-N-sulfonylaziridines via C-N bond cleavage with nucleophiles is presented. This includes the [3 + 2] annulations with (hetero)aromatic aldehydes and 1,3-disubstituted indoles, asymmetric Friedel-Crafts type reaction with electron-rich (hetero)arenes, and asymmetric aminolysis with amines, providing facile access to chiral 1,3-isoxazolidines, pyrroloindolines, 2-(hetero)arylphenethylamines, and vicinal diamines. This method features a simple and cheaply available complex of Cu(I)-chiral BINAP catalyst, excellent yield and high diastereo- and enantioselectivities, and mild reaction conditions. A mechanism involving type I dynamic kinetic asymmetric transformations (DyKATs) of the racemic aziridines is proposed based on the results of control experiments.

Correction to: Nickel-catalyzed enantioselective reductive cross-coupling of styrenyl aziridines (Journal of the American Chemical Society (2017) 139 (5688-5691) DOI: 10.1021/jacs.7b03448)

Table of Contents. The enantiomer of the BiOx ligand that delivers the indicated absolute configuration of product is (R,R)-(4-heptyl)BiOx. The corrected graphic is shown below: Page 5690. The absolute configuration of ligand L7 (4-heptyl- BiOx) was misas

Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines

A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows

Chiral Cu(salen)-Based Metal-Organic Framework for Heterogeneously Catalyzed Aziridination and Amination of Olefins

A homochiral 3D porous metal-organic framework was assembled from a chiral dicarboxylic acid-functionalized Cu(salen)-based catalyst and could serve as an efficient heterogeneous catalyst for aziridination and allylic amination of olefins. Besides easy separation and reuse of the catalyst, the chiral framework confinement could impart substrate size selectivity, enhance catalyst activity, and induce product enantioselectivity.

Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines

The metal-free synthesis of 2-substituted and 2,3-disubstituted morpholines through a one-pot strategy is described. A simple and inexpensive ammonium persulfate salt enables the reaction of aziridines with halogenated alcohols to proceed via an SN2-type ring opening followed by cyclization of the resulting haloalkoxy amine.

Regioselective Ring-Opening Nucleophilic Addition of Aziridines through Photoredox Catalyst

A mild and efficient procedure was developed for the regioselective ring-opening nucleophilic addition reactions of aziridines via visible light photoredox catalysis, that provides a practical synthetic access to 1,2-bifunctional compounds. Furthermore, the regioselective synthesis of non-racemic amino ethers from chiral aziridine could also be achieved under mild conditions. Finally, a possible reaction mechanism was proposed and further supported by control experiments.

Iron(iii) tetrakis(pentafluorophenyl)porpholactone catalyzes nitrogen atom transfer to CC and C-H bonds with organic azides

We have demonstrated that iron porpholactones could be effective catalysts for nitrogen atom transfer reactions such as aziridination of alkenes and amidation of alkanes using organic azides.

Nickel-catalyzed negishi alkylations of styrenyl aziridines

A nickel-catalyzed cross-coupling reaction between N-sulfonyl aziridines and organozinc reagents is reported. The catalytic system comprises an inexpensive and air-stable Ni(II) source and dimethyl fumarate as ligand. Regioselective synthesis of β-substituted amines is possible under mild and functional-group-tolerant conditions. The stereoselectivity of the reaction is consistent with a stereoconvergent mechanism wherein the sulfonamide directs C-C bond formation.