158109-77-4

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 188447-91-8 (S)-p-toluenesulfinimide 
• 1279697-25-4 (2R,4S)-4-Benzyl-5,5-dimethyl-3-tosyl-1,2,3-oxathiazolidine 2-oxide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 1022081-85-1 N-[(1S)-2-hydroxy-2-methyl-1-(phenylmethyl)propyl]-4-methylbenzenesulfonamide 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 874-90-8 4-methoxybenzonitrile 

Downstream Products

• 406502-75-8 dimethyl (S_S,1S,2R)-(+)-1-chloro-2-(p-methoxyphenyl)-2-(p-toluene-sulfinamide)-ethylphosphonate 
• 852332-90-2 [1R,2S,(S)S]-N-{1-(p-methoxyphenyl)-2-[(S)-2-(p-toluenesulfinyl)phenyl]-2-(methylthio)ethyl}-p-toluenesulfinamide 
• 406502-82-7 dimethyl (2S)-(-)-3-(p-methoxyphenyl)-2H-azirine 2-phosphonate 
• 406502-81-6 dimethyl (2R)-(+)-2-(p-methoxyphenyl)-2H-azirine 3-phosphonate 
• 406502-79-2 dimethyl (2S,3R)-(-)-3-(p-methoxyphenyl)aziridine-2-phosphonate 

Relevant academic research and scientific papers

Multicomponent synthesis of chiral sulfinimines

Two oxathiozolidine-S-oxide templates have been developed and used in a four-component coupling protocol for the synthesis of a wide range of chiral sulfinimines in high enantiomeric excesses. The templates can be synthesized from cheap commodity chemicals in three steps in high yields. Furthermore the template is easily recovered in high yields for recycling.

A facile synthesis of N-sulfinylaldimines

A simple and efficient procedure for the synthesis of N-sulfinylaldimines (sulfinimines) from sulfinamides and aldehydes is described. The reaction was carried out in the presence of t-BuOK or NaOH. The method is applicable for the synthesis of optically active sulfinimines.

Synthesis of enantiopure sulfinimines (Thiooxime S-oxides) catalyzed by Yb(OTf)3 from p-toluenesulfinamide and aldehydes in mild reaction conditions

(Chemical Equation Presented) Enantiomerically pure sulfinimines as important building blocks in the asymmetric synthesis of amine derivatives are prepared in good to excellent yields from chiral p-toluene-sulfinamide with aromatic, heteroaromatic, and al

Highly diastereoselective addition of ketone enolates to N-sulfinyl imines: Asymmetric synthesis of syn- and anti-1,3-amino alcohol derivatives

Lithium enolates derived from ketones may be added to N-sulfinyl imines with high diastereoselectivity. Diastereoselective reduction gave either the syn- or anti-1,3-amino alcohol derivative.

Synthesis of Sulfinimines by Direct Condensation of Sulfinamides with Aldehydes Using Cs2CO3 as an Activating and Dehydrating Reagent

Chiral sulfinimines were prepared from chiral sulfinamides and aldehydes in CH2Cl2 in the presence of cesium carbonate as an amine-activating and dehydrating reagent.

Asymmetric Synthesis Properties of Sulfinimines (Thiooxime S-Oxides)

Enantiomerically pure sulfinimines (thiooxime S-oxides 10), important building blocks in the asymmetric synthesis of amine derivatives, are prepared in good to excellent yields in one step from aromatic, heteroaromatic, and aliphatic aldehydes. This protocol involves treating commercially available (R)- or (S)-menthyl p-toluenesufinate (Andersen reagent 4) with LiHMDS, followed by the aldehyde, affording (E)-10 exclusively. The sulfinimines 10 are formed via a Peterson-type olefination reaction of silylsulfinamide anion 13 with the aldehyde. Anion 13 is generated by reaction of lithium menthoxide (12a) with bis(trimethylsilyl)sulfinamide 11, which is formed in the reaction of 4 with LiHMDS. The other product formed is O-(trimethylsilyl)menthol (12c), which is isolated in >80% yield for recycling. Two other less efficient methods for the asymmetric synthesis of 10 are discussed: (i) the asymmetric oxidation of sulfenimines 6 with chiral nonracemic oxaziridines and (ii) the reaction of metal aldimines, prepared from nitriles, with 4. All of these protocols fail with ketones.

Asymmetric synthesis of sulfinimines: Chiral ammonia imine synthons

Two Andersen-type procedures for the preparation of enantiopure sulfinimines 1 (R=H) in better than 95% ee from nitriles and aldehydes are described.