147454-97-5

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 
• 50-00-0 formaldehyd 
• 62-53-3 aniline 
• 103-01-5 N-Phenylglycine 
• 88933-19-1 methoxymethylphenylamine 
• 114838-64-1 O-pivaloyl-N-phenylhydroxilamine 
• 140-88-5 ethyl acrylate 
• 82461-60-7 N-benzoyloxy-N-phenylhydroxylamine 

Relevant academic research and scientific papers

A new synthesis of aziridine-2-carboxylates: Reaction of hexahydro- 1,3,5-triazines or N-methoxymethylanilines with alkyl diazoacetates in the presence of Lewis acid

Aziridine-2-carboxylates were prepared from the reaction of hexahydro- 1,3,5-triazines or N-methoxymethylanilines with alkyl diazoacetates in the presence of Lewis acid catalyst in high yield.

A Nanovessel-Catalyzed Three-Component Aza-Darzens Reaction

It has been previously demonstrated that nanovessels can be highly competent catalysts providing high rate accelerations and unique selectivity to the organic transformations which they mediate. However, for supramolecular assemblies to be considered a standard reagent in organic synthesis they must first demonstrate the ability to catalyze increasingly complex transformations. Herein, we report a three-component Aza-Darzens reaction that generates N-phenylaziridines, catalyzed by a supramolecular host, that provides the stereoisomer opposite to the one generated in bulk solution (trans vs cis). This transformation constitutes a rare catalytic three-component coupling within a supramolecular assembly, providing a supramolecular solution to a synthetically challenging transformation.

Synthesis of aziridines by visible-light induced decarboxylative cyclization of N-aryl glycines and diazo compounds

A visible-light induced decarboxylative aza-Darzens reaction between N-aryl glycines and diazo compounds was developed, which affords various mono-substituted aziridines in good yields.

Metal-catalysed reactions of imines with ethyl diazoacetate leading to aziridines

The metal-catalysed aziridination of imines with ethyl diazoacetate as the carbene fragment donor using various Lewis acids as the catalyst has been investigated. The catalytic properties of different Lewis acid complexes have been tested and it has been found that both main-group complexes, such as BF3·OEt2, early- and late-transition metal complexes, such as TiCl2(O-Pr1)2, Cu(OTf)2 and Zn(OTf)2 and rare-earth metal complexes, such as Yb(OTf)3, can catalyse the formation of aziridines. The aziridination gives mainly the cis-aziridines as the major diastereoisomer, but the selectivity is dependent on the substrate, catalyst and solvent. Zn(OTf)2 and Yb(OTf)3 have been shown to be general catalysts for the formation of various aziridines using different imines and a variety of reaction conditions. Both Zn(OTf)2 and Yb(OTf)3, as well as some of the other Lewis acids, in combination with various chiral ligands, have been tested as catalysts for the formation of optically active aziridines, but only low ees are obtained. The Zn(OTf)2- and Yb(OTf)3-catalysed reactions have been investigated for imines having both electron-donating and -withdrawing substituents, and in reactions containing diethyl fumarate as a trapping reagent, in attempts to obtain insight into the mechanism of the aziridination.

A new synthesis of aziridine-2-carboxylates by reaction of hexahydro-1,3,5-triazines with alkyldiazoacetates in the presence of tin(IV) chloride

Aziridine-2-carboxylates were prepared from the reaction of hexahydro-1,3,5-triazines with alkyldiazoacetates in the presence of Lewis acid catalyst in high yield.

Catalytic Formation of Aziridines from Imines and Diazoacetates

A catalytic method for the preparation of aziridines from imines and diazoacetate is developed using copper complexes as catalyst; the synthetic, diastereo- and enantio-selective scope of the reaction are presented.

N-Hydroxy-N-pivaloylanilines: a New Aziridinating Agent

An efficient synthesis of 2-functionalised N-arylaziridines from hydroxamic acids and electron deficient olefins is described.