160751-26-8

Upstream product

• 96-32-2 bromoacetic acid methyl ester 
• 160751-25-7 (S)-(-)-N-<(p-methylthio)benzylidene>-p-toluenesulfinamide 

Downstream Products

• 4302-89-0 (1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 23150-35-8 (R*,R*)-(+)-thiomicamine 
• 15318-45-3 thiamphenicol 
• 160751-27-9 (2S,3S)-2-hydroxymethyl-3-(4-methylthiophenyl)-1H-aziridine 

Relevant academic research and scientific papers

Asymmetric synthesis of the antibiotic (+)-thiamphenicol using cis-N-(p-toluenesulfinyl)aziridine 2-carboxylic acids

A concise, highly efficient asymmetric synthesis of aminopropanediol (1R,2R)-(-)-3, precursor to the broad spectrum antibiotics thiamphenicol/florfenicol 1/2, was prepared in two steps from cis-aziridine 2-carboxylic acid (2S,3S)-(-)-5.

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.