81801-27-6

Upstream product

• 177265-17-7 C₁₅H₁₅NS 
• 103-19-5 di(p-tolyl) disulfide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 6873-55-8 p-tolylsulfinyl amide 
• 98-86-2 acetophenone 
• 672-78-6 methyl p-toluene sulfinate 
• 100-47-0 benzonitrile 

Downstream Products

• 37754-48-6 (R,S_S)-N-α-methylbenzyl-p-tolylsulfinamide 
• 177468-95-0 (R,R_S)-N-α-methylbenzyl-p-tolylsulfinamide 
• 1283154-36-8 N-(1-(dimethyl(phenyl)silyl)-1-phenylethyl)-4-methylbenzenesulfonamide 
• 24865-83-6 (E)-1-phenyl-N-tosylethanimine 
• 24865-83-6 4-methyl-N-(1-phenylethylidene)benzenesulfonamide 

Relevant academic research and scientific papers

Verkade's Superbase as an Organocatalyst for the Strecker Reaction

Proazaphosphatranes -Verkade's superbases- proved to be efficient organocatalysts for the Strecker reaction between protected imines and trimethylsilyl cyanide (TMSCN). Excellent to quantitative yields were reached and, compared to other systems, only low

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.

Asymmetric synthesis of amines using a chiral, non-racemic, benzylidene sulfinamide derived from a recoverable precursor

The homochiral cyclic sulfinamide S(S)R-(+)-1 has been employed for the asymmetric synthesis of α-substituted benzylamines via the benzylidene sulfinamides R(S)R-(-)-4. Following diastereoselective reduction and hydrolysis S(S)R-(+)-1 can be recycled in one step from the sulfinic acid 11. The addition of zinc(II) bromide reverses the diastereoselectivity of the diisobutylaluminium hydride (DIBAL) reduction of the substrates 4. The same reversal is not observed in the reactions of analogues lacking an amide side chain. In one case the required benzylidene sulfinamide exists in the form of an enamine 15, the X-ray crystallographic structure of which is also featured. A second approach to chiral amines, via the addition of Grignard reagents to sulfinylamines derived from S(S)R-(+)-1, is also described.

Asymmetric Induction in the Reduction of Optically Active N-Alkylidenesulphinamides by Metal Hydrides. A New, Efficient Enantioselective Route to Chiral Amines

A series of racemic and optically active N-alkylidenesulphinamides has been prepared and their reduction by metal hydrides studied.The extent of asymmetric synthesis mainly depends on the nature of the reducing species; the best results (up to 92percent of stereoselectivity) are obtained with alkoxy-lithium aluminium hydrides.A new, highly enantioselective synthesis of amines is described.