127053-48-9

Upstream product

• 119628-74-9 trans-(4S^*,5R^*)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 
• 124994-14-5 cis-N-(p-tolylsulfonyl)-2-carbomethoxy-3-phenylaziridine 
• 21770-48-9 methyl 2,3-dibromo-3-phenylpropanoate 
• 500130-99-4 methyl (Z)-3-phenyl-2-trifluoromethylsulfonyloxy propenoate 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 119628-74-9 cis-(4S^*,5S^*)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 
• 19190-80-8 methyl trans-3-phenylglycidate 
• 100-52-7 benzaldehyde 
• 127127-36-0 cis-(4R,5R)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 
• 124-41-4 sodium methylate 
• 115794-67-7 methyl (2R,3S)-3-phenylglycidate 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 129939-41-9 Sodium (-)-(2R,3S)-E-3-phenyl oxirane-2-carboxylate 
• 121-39-1 ethyl 3-phenylglycidate 

Downstream Products

• 141241-00-1 Methyl (2R^*,3S^*)-2-amino-3-(indol-3-yl)-3-phenylpropanoat 
• 80612-97-1 (Z)-methyl 2-amino-3-phenylacrylate 
• 140429-60-3 methyl 1-chloro-trans-3-phenylaziridine-2-carboxylate 
• 140429-64-7 methyl 1-bromo-trans-3-phenylaziridine-2-carboxylate 
• 141240-93-9 (2S,3S)-3-Amino-2-chloro-3-phenyl-propionic acid methyl ester; hydrochloride 
• 142619-26-9 trans-3-phenylaziridine-2-carboxylic acid 
• 129867-24-9 (2S,3R)-1-(Biphenyl-4-carbonyl)-3-phenyl-aziridine-2-carboxylic acid methyl ester 
• 19185-82-1 Methyl (2R^*,3R^*)-2-(acetylamino)-3-hydroxy-3-phenylpropanoate 
• 141241-04-5 Methyl 1-(benzyloxycarbonyl)-trans-3-phenylaziridine-2-carboxylate 
• 141241-05-6 Methyl (2R^*,3S^*)-3-chloro-3-phenyl-2-(tosylamino)propanoate 
• 19185-82-1 Methyl (2R^*,3S^*)-2-(acetylamino)-3-hydroxy-3-phenylpropanoate 

Relevant academic research and scientific papers

Exploiting the chemistry of strained rings: Synthesis of indoles via domino reaction of aryl iodides with 2 H-azirines

(Equation Presented). The highly strained 2H-azirine ring system has been the source of considerable theoretical and synthetic work. The reaction of these strained heterocycles with transition metals has been documented to give rise to ring opening and subsequent formation of varied heterocycles. An interesting domino reaction is described wherein the strained bicyclic alkene, norbornene, mediates the reaction of 2H-azirines with aryl iodides under palladium catalysis to provide indole or polycyclic dihydroimidazole heterocycles.

Lewis acid-Lewis acid heterobimetallic cooperative catalysis: Mechanistic studies and application in enantioselective Aza-Michael reaction

The full details of a catalytic asymmetric aza-Michael reaction of methoxylamine promoted by rare earth-alkali metal heterobimetallic complexes are described, demonstrating the effectiveness of Lewis acid-Lewis acid cooperative catalysis. First, enones we

Reaction of vinyl triflates of α-keto esters with primary amines: Efficient synthesis of aziridine carboxylates

Vinyl triflates of α-keto esters react smoothly with primary amines to provide aziridine carboxylates in good yields. In all cases, little or no stereoselectivity was observed. A mechanistic study has shown that aziridine carboxylates are strictly formed

On the effect of ring substituents in the carbonylation of aziridines

The effect of ring substituents on the cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to β-lactams has been investigated. A variety of aziridines with different substituents and stereochemistry has been synthesized and subjected to carbonylation. The ring expansion to β-lactam takes place in the absence of an electron-withdrawing substituent and higher yields are always obtained for cis-aziridines. Moreover, the regioselectivity of the reaction is affected by the nature of substituents at ring carbon atoms.

A convenient synthesis of aziridine-2-carboxylic esters

Optically active oxirane-2-carboxylic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide.The azido alcohols obtained were subsequently converted into aziridine-2-carboxylic esters by reaction with triphenylphosphine, in good yields and with high optical purity.Various racemic oxirane-2-carboxylic esters were subjected to the same sequence of reactions.

Conversion of aziridine-2-carboxylic esters into 2H-azirine-2-carboxylic esters

Aziridine-2-carboxylic esters 1 were converted into 2H-azirine-2-carboxylic esters 4 in two steps.Treatment of 1 with tert-butyl hypochlorite in ether gave smooth N-chlorination.Reaction of N-chloroaziridines 2 with 1,8-diazabicycloundec-7-ene (DBU

Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1H-aziridine-2-carboxylate

Sodium -E3-phenylglycidate (±)-2E was prepared using the Darzens' procedure. Classical resolution with 1-phenylethylamine afforded optically pure salts (+)-(2S,3R)-2E and (-)-(2R,3S)-2E. Alternatively, (±)-2E was converted into (±)-2Z by ring opening of ethyl ester (±)1E with hydrogen bromide, followed by recyclization and saponification. Classical resolution of (±)-2Z with ephedrine afforded optically pure salts (+)-(2S,3S)-2Z and (-)-(2R,3R)-2Z Treatment of the four sodium salts with sodium azide followed by esterification gave hydroxy azido esters 3, which were finally converted into the four homochiral stereoisomers of methyl 3-phenyl-1H-aziridine-2-carboxylate 5 in a reaction with triphenylphosphine and subsequent heating of the initially formed oxazaphospholidines 4.