65440-68-8

Usage

InChI:InChI=1/C15H15NOS/c1-12-8-10-15(11-9-12)18(17)16-13(2)14-6-4-3-5-7-14/h3-11H,1-2H3/b16-13+/t18-/m0/s1

Upstream product

• 917-54-4 methyllithium 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 100-47-0 benzonitrile 
• 177265-17-7 C₁₅H₁₅NS 
• 98-86-2 acetophenone 
• 188447-91-8 (S)-p-toluenesulfinimide 

Downstream Products

• 250378-57-5 cis-(S_S,2S,3S)-(-)-N-p-toluenesulfinyl-2-carbomethoxy-3-methyl-3-phenylaziridine 
• 737777-08-1 (S)-N-[(1S,S_s)-1-methyl-1-phenyl-2-(p-tolylsulfinyl)ethyl]-p-toluenesulfinamide 
• 866993-65-9 [2R,3S,(S)S]-N-{2-phenyl-3-triisopropylsilyloxy-3-[(S)-2-(p-toluenesulfinyl)phenyl]propyl}-p-toluenesulfinamide 
• 913625-47-5 (R)-diethyl 2-amino-1,1-difluoro-2-phenylpropylphosphonate 
• 25488-25-9 (2S,3S)-methylphenylalanine 
• 250378-51-9 cis-(2S,3S)-(-)-N-(p-toluenesulfonyl)-2-carbomethoxy-3-methyl-3-phenylaziridine 
• 250378-52-0 methyl (2S,3S)-(-)-2-N-(p-toluenesulfonyl)amino-3-phenylbutyrate 
• 131154-18-2 (R)-(1-methyl-1-phenyl-but-3-enyl)amine 
• 131154-21-7 ((R)-2-[1,3]Dithian-2-yl-1-methyl-1-phenyl-ethyl)-carbamic acid methyl ester 
• 131154-20-6 ((R)-1-Methyl-3-oxo-1-phenyl-propyl)-carbamic acid methyl ester 
• 131154-22-8 ((R)-1-Methyl-1-phenyl-propyl)-carbamic acid methyl ester 
• 131154-19-3 ((R)-1-Methyl-1-phenyl-but-3-enyl)-carbamic acid methyl ester 

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.

Asymmetric synthesis of quaternary alpha-amino phosphonates using sulfinimines.

The addition of lithium diethylphosphonate to enantiopure ketosulfinimines is highly diastereoselective (>95%), affording the first examples of quaternary alpha-alkyl alpha-amino (arylmethyl)phosphonates.

Asymmetric Synthesis Properties of Sulfinimines (Thiooxime S-Oxides)

Enantiomerically pure sulfinimines (thiooxime S-oxides 10), important building blocks in the asymmetric synthesis of amine derivatives, are prepared in good to excellent yields in one step from aromatic, heteroaromatic, and aliphatic aldehydes. This protocol involves treating commercially available (R)- or (S)-menthyl p-toluenesufinate (Andersen reagent 4) with LiHMDS, followed by the aldehyde, affording (E)-10 exclusively. The sulfinimines 10 are formed via a Peterson-type olefination reaction of silylsulfinamide anion 13 with the aldehyde. Anion 13 is generated by reaction of lithium menthoxide (12a) with bis(trimethylsilyl)sulfinamide 11, which is formed in the reaction of 4 with LiHMDS. The other product formed is O-(trimethylsilyl)menthol (12c), which is isolated in >80% yield for recycling. Two other less efficient methods for the asymmetric synthesis of 10 are discussed: (i) the asymmetric oxidation of sulfenimines 6 with chiral nonracemic oxaziridines and (ii) the reaction of metal aldimines, prepared from nitriles, with 4. All of these protocols fail with ketones.

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.