172265-18-8

Upstream product

• 78-94-4 methyl vinyl ketone 
• 41085-71-6 bromamine T 
• 104504-02-1 4-methyl-N-(tosyloxy)benzenesulfonamide 
• 110-00-9 furan 
• 1605276-53-6 1-tosyl-2-(1-(triethylsilyloxy)vinyl)aziridine 
• 127-65-1 chloroamine-T 
• 473-34-7 N,N-dichloro-p-toluenesulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 

Downstream Products

• 82125-95-9 4-methyl-N-(3-oxobutyl)benzenesulfonamide 
• 1605276-53-6 1-tosyl-2-(1-(triethylsilyloxy)vinyl)aziridine 
• 585529-12-0 2-(1-phenylvinyl)-N-tosylaziridine 
• 1075183-25-3 2-(1-(t-butyldimethylsilyloxy)vinyl)-N-tosylaziridine 
• 54972-27-9 3-(p-tosylamino)butan-2-one 

Relevant academic research and scientific papers

One-pot stereoselective synthesis of anti 3-alkyl and 3-aryl-N-p-tosyl- aziridine-2-ketones and 3-aryl-N-p-tosyl-aziridine-2-carboxylates

An efficient and practical synthesis of N-p-tosyl-aziridine-2-ketones and carboxylates through the use of α,β-unsaturated esters and ketones has been reported. The synthesis was conducted via a one-pot procedure consisting of aminohalogenation and in situ intramolecular SN2 substitution. Triethylamine was found to be an effective base for the in situ cyclization for most substrates. Interestingly, for several enone cases, a slightly modified procedure in which 1.0 equivalent of p-TsNCl2 was slowly added into 2.0 equivalents of enone for aminohalogenation followed by quenching with aqueous Na2SO3 resulted in crude aziridines which were proven to be nearly pure by the crude 1H NMR analysis. Moderate to good yields and excellent anti stereoselectivity were achieved for 21 examples.

A Bulky Thiyl-Radical Catalyst for the [3+2] Cyclization of N-Tosyl Vinylaziridines and Alkenes

Thiyl-radical-catalyzed cyclization reactions of N-tosyl vinylaziridines and alkenes were developed as a new synthetic method for the generation of substituted pyrrolidines. The key to making this process accessible to a broad range of substrates is the use of a sterically demanding thiyl radical, which prevents the undesired degradation of the catalyst.

The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(I)-Catalyzed Intermolecular Cycloadditions of Vinyl Aziridines and Alkynes

Catalyst-controlled divergent intermolecular cycloadditions of vinylaziridines with alkynes have been developed. By using [Rh(NBD)2]BF4 as the catalyst, a [3 + 2] cycloaddition reaction was achieved with broad substrate scope and high stereoselectivity under mild reaction conditions. Moreover, the chirality of vinylaziridines can be completely transferred to the [3 + 2] cycloadducts. When the catalyst was changed to [Rh(η6-C10H8) (COD)]SbF6, the alternative [5 + 2] cycloadducts were selectively formed under otherwise identical conditions.

Intermolecular (4+3) cycloadditions of aziridinyl enolsilanes

Upon activation by strong Bronsted acids, aziridinyl enolsilanes undergo (4+3) cycloadditions with dienes to afford aminoalkylated cycloheptenones as products. The use of a highly polar medium such as nitroalkane facilitates high cycloaddition yields of up to 99%. Optically pure aziridinyl enolsilanes react to yield (4+3) cycloadducts with up to 99% ee.

Palladium(II) mediated aziridination of olefins with bromamine-T as the nitrogen source: scope and mechanism

The palladium(II)-promoted reaction of a variety of olefins and bromamine-T provided N-tosyl-2-substituted aziridines under mild conditions. Olefins bearing chiral appendages gave only a poor to modest diastereoselectivity. Appropriate deuterated olefins

A practical, fast, and high-yielding aziridination procedure using simple Cu(II) complexes containing N-donor pyridine-based ligands

Four-coordinate dichlorocopper(II) complexes derived from di(2-pyridyl)methanes or pyridine itself exhibit high catalytic activity in aziridination of regular olefins with PhINTs in weakly coordinating chloroform in the presence of 1-2 equiv of NaBAr

Palladium(II)-promoted aziridination of olefins with bromamine T as the nitrogen transfer reagent

The palladium(II)-promoted reaction of a variety of olefins and bromamine T, as the nitrogen atom transfer reagent, provided N-tosyl-2-substituted aziridines under mild conditions.

Pyridinium hydrobromide perbromide: A versatile catalyst for aziridination of olefins using chloramine-T

Formula presented Pyridinium hydrobromide perbromide (PyHBr3) catalyzes effectively the aziridination of electron-deficient as well as electron-rich olefins using Chloramine-T (N-chloro-N-sodio-p-toluenesulfonamide) as a nitrogen source to afford the corr

Reduction of 2-acylaziridines by samarium(II) iodide. An efficient and regioselective route to β-amino carbonyl compounds

A convenient method for the reduction of 2-acylaziridines, aziridine-2- carboxylates and aziridine-2-carboxamides is described. The reduction of all of the substrates examined was extremely rapid and highly regioselective, giving rise to β-amino carbonyl compounds. This method appears to be general for all of the classes of aziridines mentioned above, and also tolerates a variety of nitrogen protecting groups.