31907-94-5

Upstream product

• 78-94-4 methyl vinyl ketone 
• 622-79-7 benzyl azide 
• 25109-57-3 3,4-dibromobutan-2-one 
• 100-46-9 benzylamine 
• 61203-01-8 3-bromobut-3-en-2-one 
• 1326628-20-9 1-benzyl-N-methoxy-N-methylaziridine-2-carboxamide 
• 75-16-1 methylmagnesium bromide 
• 34943-06-1 1-benzylaziridine-2-carboxylic acid ethyl ester 

Downstream Products

• 1359843-41-6 C₁₇H₂₇NOSi 
• 1359843-40-5 1-benzyl-2-(prop-1-en-2-yl)aziridine 

Relevant academic research and scientific papers

Bronsted acid-promoted olefin aziridination and formal anti-aminohydroxylation

A straightforward synthesis of aziridines is reported from an electron-rich azide (alkyl or aryl azide), electron-deficient olefin, and triflic acid in cold acetonitrile. The only coproduct of the reaction is dinitrogen (N2). Active ester substrates bearing a nucleophilic carbonyl engage the putative protonated aziridine intermediate to produce the product of olefin aminohydroxylation in which the nitrogen is benzyl protected and the oxygen is acylated. The possibility that a triazoline need not be an intermediate in aziridine production is advanced. Copyright

A Remarkably Efficient Phase-Transfer Catalyzed Amination of α -Bromo- α, β -Unsaturated Ketones in Water

Tandem conjugate addition-alkylation reaction of various amines with α-bromo-α, β-unsaturated ketones resulted in near-quantitative conversions into the corresponding aziridines when the reaction was carried out in the presence of 10 mol% of phase-transfer, PT catalysts in water. Some chiral quaternary ammonium salts derived from Cinchona alkaloids were investigated as water-stable PT catalysts. The scope and limitations of the reaction have also been investigated. The catalytic performances were significantly improved in comparison with the corresponding ordinary quaternary ammonium salt catalysts, and excellent yields (81%-96%) were obtained. Although an increase in the rate of aziridination has been accomplished, no stereoselectivity was observed. The positive values of the protocol have been confirmed.

A Metal-Free Domino Process for Regioselective Synthesis of 1,2,4-Trisubstituted Pyrroles: Application toward the Formal Synthesis of Ningalin B

A new one-pot, transition-metal, acid/base-free domino process is developed for the regioselective synthesis of 1,2,4-trisubstituted pyrroles. The process involves 1,3-dipolar cycloaddition of unsymmetrical azomethine ylide resulting from the thermal C-C bond cleavage of unactivated aziridines with β-bromo-β-nitrostyrene, followed by a cascade of elimination and aromatization reaction sequence to preferentially furnish 1,2,4-trisubstituted pyrroles instead of the expected 1,2,3-trisubstituted pyrroles, in good to excellent yields. Further, the application of the methodology for the formal synthesis of ningalin B is delineated.

Nucleophilic trifluoromethylation of aziridinyl ketones: A convenient access to fluorinated aziridinyl alcohols

A convenient synthesis of α-(aziridin-2-yl)-α-(trifluoromethyl) alcohols starting with ethyl aziridine-2-carboxylates is reported. Grignard reaction with the corresponding Weinreb amides led to aziridin-2-yl ketones, and subsequent treatment with Ruppert-Prakash reagent gave the trimethylsilylated target compounds as mixtures of diastereoisomers, which were desilylated with TBAF. In the case of ethyl 1-((S)-1-phenylethyl)aziridine-2-carboxylate, (S,S)- and (S,R)-aziridin-2-yl ketones were obtained, separated chromatographically and transformed into the desired enantiomerically pure α-trifluoromethylated alcohols.