84024-60-2

Upstream product

• 87439-84-7 ethyl 2,3-dichloro-3-phenylpropenoate 
• 138478-36-1 R*S* 1-benzoyl-2-methoxycarbonyl-3-phenylaziridine 
• 105-53-3 diethyl malonate 
• 121-39-1 ethyl 3-phenylglycidate 
• 133038-44-5 [(benzylidene)amino]acetic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 908094-04-2 phenyldiazomethane 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 

Downstream Products

• 84033-37-4 (2R,3S)-1-((Z)-2-Ethoxycarbonyl-vinyl)-3-phenyl-aziridine-2-carboxylic acid ethyl ester 
• 6436-90-4 ethyl 2-(benzylamino)acetate 
• 6335-76-8 3-amino-3-phenylpropionic acid ethyl ester 
• 475640-21-2 (2S,3R)-3-Phenyl-1-{(S)-1-[(E)-(3-phenyl-acryloyl)]-pyrrolidine-2-carbonyl}-aziridine-2-carboxylic acid ethyl ester 
• 863311-92-6 ethyl 2-(4-chloro-[1,2,3]-dithiazol-5-ylideneamino)-3-phenylacrylate 
• 919101-04-5 6-phenyl-2-(3-phenylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol 
• 84033-38-5 (Z)-2-((2S,3R)-2-Ethoxycarbonyl-3-phenyl-aziridin-1-yl)-but-2-enedioic acid dimethyl ester 
• 97938-69-7 ethyl 1-benzyl-2,4-diphenyl-4,5-dihydro-1H-imidazole-5-carboxylate 
• 101719-48-6 ethyl 3-(4-methylphenylsulfonamido)-3-phenylpropanoate 
• 136159-62-1 tert-butyl ethyl N-benzyl-N-(tert-butoxycarbonyl)glycinate 
• 7554-23-6 ethyl 3-acetamido-3-phenylpropanoate 
• 330636-99-2 (S)-4-Methyl-2-[((2S,3R)-3-phenyl-1-{(S)-1-[(E)-(3-phenyl-acryloyl)]-pyrrolidine-2-carbonyl}-aziridine-2-carbonyl)-amino]-pentanoic acid methyl ester 

Relevant academic research and scientific papers

A catalytic synthesis of aziridines without the usual byproducts

Complementary to existing routes, the Lewis acid catalyzed reactions of phenyldiazomethane with α-imino esters selectively produce cis-aziridine-2-carboxylates without competitive formation of enamino ester or carbene dimer byproducts. Georg Thieme Verlag

Enantiopure trans -3-arylaziridine-2-carboxamides: Preparation by bacterial hydrolysis and ring-openings toward enantiopure, unnatural D -α-amino acids

Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural d-α- aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.

Amphoteric amino aldehydes enable rapid assembly of unprotected amino alcohols

(Chemical Equation Presented) Apples and oranges: The term "amphoteric" is derived from the Greek "amphoteros", which literally means "both of two". Amphoteric amino aldehydes are counterintuitive molecules in that they contain both electrophilic and nucl

Aziridines as templates: A general strategy for the stereospecific synthesis of 2-azetidinones

Various routes to a variety of azridine-2-carboxylates have been described and the stereochemistry of these compounds has been determined by spectroscopic methods. Further, greater diversity of β-lactams via ring expansion of these azridines-2-carboxylates were obtained by a general, efficient and direct stereospecific approach.

Readily available unprotected amino aldehydes

We report a new class of bench-stable compounds that contain seemingly incompatible functional groups: an aldehyde and an unprotected secondary amine. The thermodynamic driving force to undergo condensation between these two functionalities is offset by a

Stereoselective synthesis of β-substituted phenylalanine-β-phenylisoserine-derived tripeptides using N-cinnamoyl-L-proline as template: Synthesis of structural analogues of HIV protease inhibitors

N-Cinnamoyl-L-proline can be used as a template on which β-substituted phenylalanine and β-phenylisoserine residues can be synthesized leading to tripeptide derivatives as structural analogues of HIV protease inhibitors.

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.

The Regioselectivity of the Ring Opening of 1-Activated or Nonactivated 2-Alkoxycarbonyl or 2-Cyanoaziridines by Carbanions of the Dicarbonyl Compounds

Ring opening of title compounds with alkyl malonates, acetylacetone, methyl acetylacetate, and malononitrile was studied.The regioselectivity of the opening depends on several facts.A phenyl group on C-3 favours C-3-N bond cleavage, whereas C-2-N bond cleavage is predominant with C-3-substituted or C-2-H aziridines.Cyanoaziridines are predominantly cleaved at C-3-N.The aziridine configuration at C-2 and C-3 is maintained during the cyclisation in pyrrolidones.

Reactivite des N-vinylaziridines fonctionalisees. Synthese de derives des α,β-dehydro α-amino acides

Secondary 2-cyano- and 2-ethoxycarbonylaziridines react with acetylenic compounds and activated vinylic chlorides to gives 2-cyano and 2-ethoxycarbonyl N-vinylaziridines.The nucleophile-catalysed isomerization of these compounds generally gives α,β-dehydr