20752-48-1

Upstream product

• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 188447-91-8 (S)-p-toluenesulfinimide 
• 100-47-0 benzonitrile 
• 220732-34-3 (S)-(E)-N-ethylidene-4-methylbenzenesulfinamide 
• 75-16-1 methylmagnesium bromide 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 866993-20-6 (S)-4-methyl-N-(1-phenylethylidene)benzenesulfinamide 
• 65440-68-8 [S-(E)]-(+)-N-α-methylbenzylidene-p-toluenesulfinamide 

Downstream Products

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 72984-27-1 4-Methyl-N-((R)-1-phenyl-ethyl)-benzenesulfonamide 
• 66558-04-1 N-[(1S)-1-phenylethan-1-yl]-4-methylbenzenesulfonamide 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 64396-66-3 methyl (R)-4-methylbenzenesulfinate 

Relevant academic research and scientific papers

Rare-Earth-Catalyzed Transsulfinamidation of Sulfinamides with Amines

A rare-earth-catalyzed transsulfinamidation of primary sulfinamides with alkyl, aryl, and heterocyclic amines for the synthesis of diverse secondary and tertiary sulfinamides has been realized. Unlike transition metal-catalyzed cross-coupling approaches restricted to non-commercially available disubstituted O-benzoyl hydroxylamines, this newly developed protocol is suitable for diverse readily available primary and secondary amines without any modifications. Excellent catalytic activity and selectivity are achieved with Eu(OTf)3 under mild reaction conditions, which extends the applicability of rare-earth catalysis.

Stereoselective addition to chiral p-toluene sulfinimines

Diastereoselective addition of a number of Grignard reagents to chiral p-toluene sulfinimines 2b-2d under the mediation of copper salts afforded various protected α-branched amines. (C) 2000 Elsevier Science Ltd.

Stereoselective Addition Reactions of Chiral N-Benzylidene-p-toluenesulfinamides. Asymmetric Syntheses of β- and γ-Amino Acids

Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitril with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate.Treatment of 2 with allylmagnesium bromide in ether at 0 deg C gave the adducts (R)-7 with excellent stereoselectivity.Pure chiral sulfinamides 7 were converted into β- and γ-amino acids in four and five steps, respectively.

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.