336784-74-8

Upstream product

• 695-12-5 vinylcyclohexane 
• 76152-15-3 N-iodo-N-potassio-p-toluenesulphonamide 
• 70-55-3 toluene-4-sulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 75-11-6 diiodomethane 
• 175355-34-7 N-(cyclohexylmethylene)-4-methylbenzenesulfonamide 
• 74-95-3 1,1-dibromomethane 
• 127-65-1 chloroamine-T 
• 98-59-9 p-toluenesulfonyl chloride 
• 1593-60-8 p-toluenesulfonylhydroxylamine 
• 917-54-4 methyllithium 
• 593-71-5 Chloroiodomethane 
• 260975-29-9 (E)-N-cyclohexylmethylene-4-toluenesulfonamide 

Downstream Products

• 1065519-41-6 2-cyclohexylaziridine 

Relevant academic research and scientific papers

Iron(ii)-catalyzed intermolecular aziridination of alkenes employing hydroxylamine derivatives as clean nitrene sources

The iron-catalyzed intermolecular aziridination of alkenes with hydroxylamine derivatives is described. Using simple iron(ii) sources and readily available ligands, the formal (2 + 1) cycloaddition process proved to be efficient on both styrenes and aliphatic alkenes, providing access to a wide range of aziridines. In these particularly sustainable reaction conditions, yields up to 89% could be obtained, with a catalyst loading which could be lowered to 5 mol% when the reaction was performed on large scale. Preliminary mechanistic studies suggest that both concerted and stepwise pathways are operating in this transformation. This journal is

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.

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 of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides

A photoassisted Ni-catalyzed reductive cross-coupling between tosyl-protected alkyl aziridines and commercially available (hetero)aryl iodides is reported. This mild and modular method proceeds in the absence of stoichiometric heterogeneous reductants and uses an inexpensive organic photocatalyst to access medicinally valuable β-phenethylamine derivatives. Unprecedented reactivity was achieved with the activation of cyclic aziridines. Mechanistic studies suggest that the regioselectivity and reactivity observed under these conditions are a result of nucleophilic iodide ring opening of the aziridine to generate an iodoamine as the active electrophile. This strategy also enables cross-coupling with Boc-protected aziridines.

Highly regioselective nickel-catalyzed cross-coupling of N -tosylaziridines and alkylzinc reagents

Herein, we report the first ligand-controlled, nickel-catalyzed cross-coupling of aliphatic N-tosylaziridines with aliphatic organozinc reagents. The reaction protocol displays complete regioselectivity for reaction at the less hindered C-N bond, and the products are furnished in good to excellent yield for a broad selection of substrates. Moreover, we have developed an air-stable nickel(II) chloride/ligand precatalyst that can be handled and stored outside a glovebox. In addition to increasing the activity of this catalyst system, this also greatly improves the practicality of this reaction, as the use of the very air-sensitive Ni(cod)2 is avoided. Finally, mechanistic investigations, including deuterium-labeling studies, show that the reaction proceeds with overall inversion of configuration at the terminal position of the aziridine by way of aziridine ring opening by Ni (inversion), transmetalation (retention), and reductive elimination (retention).

Enantioselective synthesis and stereoselective ring opening of N-acylaziridines

Kinetic resolution of N-acylaziridines by nucleophilic ring opening was achieved with (R)-BINOL as the chiral modifier under boron-catalyzed conditions (see scheme; Ar=3,5-dinitrophenyl). The consumed enantiomer of aziridine can be further converted to an enantioenriched 1,2-chloroamide with recovery of (R)-BINOL. Copyright

NaIO4/LiBr-mediated aziridination of olefins using chloramine-T

A new milder protocol for aziridination of a variety of olefins has been described. The process employs catalytic amount of sodium metaperiodate (NaIO4) as an oxidant and LiBr and chloramine-T as the bromine and nitrogen sources, respectively. Interestingly, the formation of aziridine products in all the cases studied takes place presumably through a process of 1,2-aminobromination of alkenes.

Addition reactions of chloro- Or iodomethyllithium to imines. Synthesis of enantiopure aziridines and β-chloroamines

We report a novel, simple, and efficient synthesis of aziridines and l-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodoor chloromethyllithium, respectively. Both halogenated anions were generated in situ by treatment of diiodo- or chloroiodomethane with methyllithium at -78 or 0 °C. The reaction of in situ generated iodoor chloromethyllithium could also be performed from chiral 2-aminoaldimines to yield enantiopure aziridines or (2S,3S)-2,3-diamino- l-chloroalkanes with high stereoselectivity.

Addition reactions of iodomethyllithium to imines. A direct and efficient synthesis of aziridines and enantiopure amino aziridines

(Chemical Equation Presented) An efficient and general synthesis of aziridines by the reaction of imines derived from p-toluenesulfonamides with in situ generated iodomethyllithium, with a simple and rapid experimental protocol, is reported for the first time. The reaction with the chiral aldimine derived from phenylalaninal allowed access to (2R,1′S)-2-(1′-aminoalkyl) aziridine with very high diastereoselectivity, in enantiopure form. A mechanism to explain this novel reaction is proposed.

Syntheses of acetonitrile ligated copper complexes with perfluoroalkoxy aluminate as counter anion and their catalytic application for olefin aziridination

Acetonitrile ligated copper complexes with perfluoroalkoxy aluminate Al {OC (CF3)3}4- as weakly coordinating counter anion are successfully synthesized. Aziridination of various olefins with PhINTs catalyzed by