37754-48-6

Upstream product

• 65440-68-8 [S-(E)]-(+)-N-α-methylbenzylidene-p-toluenesulfinamide 
• 866993-20-6 (S)-4-methyl-N-(1-phenylethylidene)benzenesulfinamide 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 672-78-6 methyl p-toluene sulfinate 
• 81801-27-6 (+/-)-(S,E)-N-(1-Phenylethylidene)toluene-p-sulfinamide 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 75-16-1 methylmagnesium bromide 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 103-19-5 di(p-tolyl) disulfide 
• 106-45-6 para-thiocresol 
• 98-86-2 acetophenone 
• 100-47-0 benzonitrile 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 72984-27-1 4-Methyl-N-((R)-1-phenyl-ethyl)-benzenesulfonamide 
• 253316-00-6 (S)-N-[(R)-1-phenylethyl]-p-toluenesulfonimidoyl chloride 

Relevant academic research and scientific papers

Application of sulfonyl chlorides and chiral amines in the efficient synthesis of nonracemic sulfinamides

A simple protocol that allows the preparation of separable epimeric sulfinamides from chiral amines and sulfonyl chlorides reduced in situ with triphenylphosphine in the presence of KOH is described. Using this method, tosyl chloride and nosyl chloride were successfully reacted with α-substituted primary amines to give five diastereomeric pairs, in certain cases accompanied by a small amount of the corresponding sulfonamide. Enantiopure products were isolated by column chromatography. The obtained enantiomerically pure sulfinamides were tested as organocatalysts in the asymmetric epoxide ring opening.

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.

Preparation of racemic and enantiopure arenesulfonimidoyl azoles - New compounds chiral on sulfur

The novel arenesulfonimidoyl imidazoles 7a-j and nitrotriazoles 9d-j were obtained in good yield from the corresponding arenesulfonimidoyl chlorides 6a-j. The reaction of optically pure sulfonimidoyl chlorides 6 with imidazole resulted in the first reported optically active arenesulfonimidoyl imidazoles 7 with high enantiomeric purities (ee up to >99%); the stereochemical course of the reaction (inversion or retention at sulfur) is shown to be strongly dependent on the aryl substituent. By contrast, the analogous reaction of optically pure compounds 6 with 3-nitro-1,2,4-triazole led to racemic arenesulfonimidoyl nitrotriazoles 9. Optically active compounds of this type, (S)-9f (ee 99%) and (R)-9f (ee 92%), were obtained by semi-preparative chiral HPLC. The optically active arenesulfonimidoyl imidazolium salt (RS,RC)-8j was prepared by diastereoselective methylation (de >90%) of the optically pure imidazole derivative (RS,RC)-7j.

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.

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.