158109-81-0

Basic information

• Product Name: cis-(2S,3S)-(+)-N-(p-toluenesulfonyl)-2-carbomethoxy-3-phenylaziridine
• Synonyms: cis-(2S,3S)-(+)-N-(p-toluenesulfonyl)-2-carbomethoxy-3-phenylaziridine
• CAS NO: 158109-81-0
• Molecular Weight: 331.392
• Mol File: 158109-81-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: cis-(2S,3S)-(+)-N-(p-toluenesulfonyl)-2-carbomethoxy-3-phenylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: cis-(2S,3S)-(+)-N-(p-toluenesulfonyl)-2-carbomethoxy-3-phenylaziridine(158109-81-0)
• EPA Substance Registry System: cis-(2S,3S)-(+)-N-(p-toluenesulfonyl)-2-carbomethoxy-3-phenylaziridine(158109-81-0)

Safety Data

• Hazardous Substances Data: 158109-81-0(Hazardous Substances Data)

Upstream product

• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 103-26-4 Methyl cinnamate 
• 127-65-1 chloroamine-T 
• 176298-46-7 2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester 
• 158009-37-1 cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine 

Downstream Products

• 34635-34-2 N-tosylphenylalanine 
• 163013-11-4 methyl trans-2-(N-(p-tolylsulfonyl)amino)cinnamate 
• 51220-86-1 N-(p-toluenesulfonyl)-L-phenylalanine methyl ester 
• 158109-82-1 Tos-D,L-Phe(β-OH)-OMe 

Relevant articles and documents

Aza-Darzens asymmetric synthesis of N-(p-toluenesulfinyl)aziridine 2- carboxylate esters from sulfinimines (N-sulfinyl imines)

The one-step aza-Darzens reaction of sulfinimines 2 with lithium α- bromoenolates readily affords diversely substituted cis and trans N- sulfinylaziridine 2-carboxylate esters 3 and 7 in good yield and excellent diastereoselectivity. Higher yields, but lower de's, result when a mixture of the α-bromo ester and 2 are treated with base. The N-sulfinyl group is transformed, nearly quantitatively, without ring opening, into the N-tosyl activating group by oxidation with m-CPBA. Selective removal of the N- sulfinyl group in aziridines 3a and 3h with TFA/H2O affords 1H-aziridines 21 which are difficult to prepared by other means. However, C(3) activated azirines such as 3b undergo ring-opening under these conditions. Alternatively, the N-sulfinyl group, even in C(3)-activated aziridines, was selectively and efficiently removed by treatment of the aziridine with 2 equiv of MeMgBr.

Aziridine compounds, methods of preparation and reactions thereof

Novel N-sulfinyl-2-carboxyaziridine compounds and novel N-hydrogen-2-hydroxymethylaziridine compounds are provided. The asymmetric synthesis of N-sulfinylaziridines is readily accomplished in high diastereomeric purity and good yield by the Darzens-type reaction of the metal enolate of an α-haloester and an enantiopure sulfinimine. Ring-opening of these aziridines affords α-amino acids and the otherwise difficult to prepare syn-β-hydroxy-α-amino acids, both key structural units found in many bioactive materials. The N-sulfinyl radical may be selectively removed from the novel aziridine compounds by treatment with acid or base. Alternatively, the N-sulfinyl radical may be oxidized to provide the corresponding N-sulfonyl-aziridine, or reduced to form the corresponding 1H-2-hydroxymethylaziridine, either of which may subsequently be ring-opened to provide precursors to bioactive compounds.