181874-01-1

Basic information

• Product Name: trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine
• Synonyms: trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine
• CAS NO: 181874-01-1
• Molecular Weight: 329.42
• Mol File: 181874-01-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine(181874-01-1)
• EPA Substance Registry System: trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine(181874-01-1)

Safety Data

• Hazardous Substances Data: 181874-01-1(Hazardous Substances Data)

Upstream product

• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 5445-17-0 Methyl 2-bromopropionate 

Downstream Products

• 181874-02-2 (R)-2-Methyl-3-phenyl-2-(toluene-4-sulfonylamino)-propionic acid methyl ester 
• 38574-55-9 (R)-(-)-methyl 2-amino-2-methyl-3-phenylpropionate 
• 17350-84-4 (R)-2-amino-2-methyl-3-phenylpropanoic acid 
• 127598-01-0 (1R,2R)-N-(3-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide 
• 193980-00-6 (2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid 
• 181874-04-4 trans-(2R,3S)-(+)-N-(p-toluenesulfonyl)-2-methyl-2-carbomethoxy-3-phenylaziridine 
• 73035-89-9 methyl (2R,3R)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoate 

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.

2-Methyl N-(p-toluenesulfinyl)aziridine-2-carboxylic acid: Asymmetric synthesis of α-methylphenylalanine and α-methyl-β-phenylserine

2-Substituted aziridine 2a, prepared from sulfinimine 1 via a Darzens-type condensation, undergoes a highly regio- and stereocontrolled ring-opening to give α-methylphenylalanine and α-methyl-β-phenylserine in high enantiomeric purity.