350479-90-2

Upstream product

• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 100-52-7 benzaldehyde 
• 100-47-0 benzonitrile 
• 50444-99-0 (1R,2S,5R)-menthyl-(S)-p-toluenesulfinate 
• 1022081-85-1 N-[(1S)-2-hydroxy-2-methyl-1-(phenylmethyl)propyl]-4-methylbenzenesulfonamide 
• 1279696-96-6 (2R,4S)-3-[(4-methylphenyl)sulfonyl]-4-(phenylmethyl)-1,2,3-oxathiazolidine 2-oxide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 4039-32-1 lithium hexamethyldisilazane 
• 1279697-25-4 (2R,4S)-4-Benzyl-5,5-dimethyl-3-tosyl-1,2,3-oxathiazolidine 2-oxide 
• 82495-70-3 (2S)-2-p-toluenesulfonamido-3-phenylpropanol 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 749253-91-6 (S_S,2S,3S)-(+)-ethyl 2-N-(diphenylmethylideneamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate 
• 930299-14-2 ethyl (S_S,2R,3S)-(+)-2-N-(diphenylmethyleneamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate 

Downstream Products

• 181874-01-1 trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine 
• 188760-07-8 methyl [(2R,4S,5S,S_S)-4-benzyl-2,5-diphenyl-1-(p-tolylsulfinyl)-1,3-imidazolidin-4-yl]carboxylate 
• 188760-06-7 (-)-methyl [(2S,4R,5R,S_S)-4-benzyl-2,5-diphenyl-1-(p-tolylsulfinyl)-1,3-imidazolidin-4-yl]carboxylate 
• 180906-52-9 [(R)-2-Phenyl-2-((S)-toluene-4-sulfinylamino)-ethyl]-phosphonic acid dimethyl ester 
• 208345-52-2 N,N-Diethyl-4-methoxy-2-[(S)-2-phenyl-2-((S)-toluene-4-sulfinylamino)-ethyl]-benzamide 
• 215439-15-9 (S_S,2S,3R) methyl 3--3-phenyl-2-vinylpropanoate 
• 267011-72-3 methyl (S_S,R)-(+)-methyl 3-oxo-5-phenyl-5-(p-toluenesulfinylamino)pentanoate 
• 280128-26-9 (S)-N-[(2R,R_S)-1-phenyl-2-p-tolylsulfinylethyl]-p-toluenesulfinamide 

Relevant academic research and scientific papers

Activation of the Si-B Linkage: Copper-Catalyzed addition of nucleophilic silicon to imines

Activation of the Si-B bond through copper-catalyzed transmetalation quickly developed into a practical method to generate Cu-Si reagents These silicon nucleophiles cleanly add to aldehyde-derived imine electrophiles to form R-silylated amines in protic media, and no carbon-tonitrogen Brook-type rearrangement of the intermediate anion is observed. Aside from electron-withdrawing groups at the imine nitrogen atom, for example, SO2Tol and P(O)Ph2, previously delicate nitrogen substituents such as phenyl or benzhydryl are tolerated. The same protocol also allows the unprecedented addition to representative ketone-derived imines.

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.

Asymmetric synthesis of anti- and syn-2,3-diamino esters using sulfinimines. Water and concentration effects

(Chemical Equation Presented) In the absence of water, an excess of the lithium enolate of N-(diphenylmethylene)glycine ethyl ester (4) adds to sulfinimines to give syn-2,3-diamino esters 6, and in the presence of water, this enolate gives the anti-2,3-diamino esters 5. These unusual results are interpreted in terms of those factors that inhibit the retro-Mannich fragmentation in the diamino esters.

Stereoselective synthesis of β-substituted β-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines

A highly stereoselective synthesis of β-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines is described. The addition reaction proceeds in good yield (75-99%) and stereoselectivity.

Asymmetric lithiation-substitution sequences of substituted allylamines

(-)-Sparteine-mediated asymmetric lithiation-substitution sequences of 2- and 3-substituted N-(Boc)-N-(p-methoxyphenyl) allylic amines with electrophiles have been investigated. Asymmetric lithiation-substitutions of N-(Boc)-N-(p-methoxyphenyl) allylic am

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.

Interesting by-products in the synthesis of chiral α- aminophosphinates from enantiopure sulfinimines

A new reaction of enantiopure sulfinimines and ethyl phenylphosphinate is given. Several unexpected products were isolated and identified, their mechanism of formation is proposed.