153277-50-0

Upstream product

• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 
• 188447-91-8 (S)-p-toluenesulfinimide 

Downstream Products

• 771478-95-6 C₃₂H₃₀N₂O₃S 
• 1268850-93-6 N-((R,Ss,E)-2-ethoxy-1-(4-methoxyphenyl)penta-2,4-dienyl)-4-methylbenzenesulfinamide 
• 1268851-05-3 (R,E)-2-ethoxy-1-(4-methoxyphenyl)penta-2,4-dien-1-amine 
• 1254107-48-6 C₂₈H₂₉NO₅S 

Relevant academic research and scientific papers

Stereocontrolled Addition of Scrambling ortho-Sulfinyl Carbanions: Easy Access to Homopropargylamines and α-Allenylamines

An unprecedented behavior of ortho-sulfinylpropargyl carbanions in the presence of optically active sulfinylimines affords two different families of compounds: This peculiar chemodivergency is importantly affected by the nature of the employed base, and a

1,8-Diazabicyclo[5.4.0]undec-7-ene-mediated formation of N-sulfinyl imines

A facile and efficient method was developed for the preparation of a variety of aryl, heteroaryl, and alkyl N-sulfinyl imines using 1,8-diazabicyclo[5.4.0]undec-7-ene. In addition to tert-butanesulfinamide, the condensation is also effective with p-toluenesulfinamide. The reaction was performed at room temperature and produces the corresponding N-sulfinyl imines in excellent yields in the absence of acids, metals, and additives. This methodology is also useful for the preparation of N-sulfinyl imines on gram scale. A one-pot synthesis was developed using aryl and heteroaryl alcohols with both tert-butanesulfinamide and p-toluenesulfinamide at room temperature, resulting in the corresponding N-sulfinyl imines with good yields.

Facile synthesis of optically pure 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines

(Figure presented) A concise high-yielding route to synthetically useful 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines in high enantiomeric purity is described. The key step of this route is the completely stereoselective addition of lithium (R)-ortho-(p-toluenesulfinyl)benzylic carbanions to (S).N.p-toluenesulfinylimines, which takes place in very high or quantitative yields. N-Desulfinyiation and C-desulfinylation of the resulting adducts can be achieved with no loss of optical purity employing conventional methods (TFA and Raney-Ni, respectively).