77382-90-2

Upstream product

• 7073-88-3 N-salicylidene-(S)-α-maphthylamine 
• 917-54-4 methyllithium 
• 10420-89-0 (S)-1-(1-Naphthyl)ethylamine 
• 118-93-4 o-hydroxyacetophenone 
• 90-02-8 salicylaldehyde 
• 77383-02-9 2-{1-[(E)-(S)-1-Naphthalen-1-yl-ethylimino]-ethyl}-phenol 

Downstream Products

• 13153-10-1 (S)-(-)-n-butyl phenyl sulfoxide 
• 78347-74-7 N-<(S)-1-(o-hydroxyphenyl)ethyl>-N-<(S)-1-α-naphthylethyl> (S^S)-phenylsulfinamide 
• 78347-74-7 N-<(S)-1-(o-hydroxyphenyl)ethyl>-N-<(S)-1-α-naphthylethyl> (S^R)-phenylsulfinamide 
• 78347-73-6 N-<(S)-1-(o-hydroxyphenyl)ethyl>-N-<(S)-1-α-naphthylethyl> (S^S)-butylsulfinamide 
• 78347-73-6 N-<(S)-1-(o-hydroxyphenyl)ethyl>-N-<(S)-1-α-naphthylethyl> (S^R)-butylsulfinamide 
• 78347-75-8 N-<(S)-1-(o-hydroxyphenyl)ethyl>-N-<(S)-1-α-naphthylethyl> (S^R)-methylsulfinamide 
• 78347-75-8 N-<(S)-1-(o-hydroxyphenyl)ethyl>-N-<(S)-1-α-naphthylethyl> (S^S)-methylsulfinamide 
• 1193-82-4 (S)-methylphenylsulfoxide 

Relevant academic research and scientific papers

Studies on Chiral Organo-Sulfur Compounds. I. Asymmetric Synthesis of Sulfoxides with Optically Active o-Aminoalkylphenol Derivatives

Several kinds of optically active o-aminoalkylphenols were prepared and used to develop asymmetric synthetic methods for chiral sulfoxides.The reaction of 2,3-dihydro-1,2,3-benzoxathiazine 2-oxides (derived from the o-aminoalkylphenols and thionyl chloride) with phenylmagnesium bromide, followed by treatment with alkyllithium, gave optically active sulfoxides with high enantiospecificity.Among several kinds of optically active o-aminoalkylphenols examined, the readily available aminophenol, (S)-(-)-o-phenol, was found to be the most efficient and recyclable chiral source for the asymmetric synthesis of sulfoxides.Keywords - asymmetric synthesis; chiral sulfoxide; o-aminoalkylphenol; 3,4-dihydro-1,2,3-benzoxathiazine 2-oxide; thionyl chloride

A HIGHLY EFFICIENT AND RECYCLABLE CHIRAL DIRECTOR FOR ASYMMETRIC SYNTHESIS OF SULFOXIDES

The benzoxathiazine 2-oxide derivatives (2a-f) were prepared by reaction of the aminophenols (1a-f) with thionyl chloride in good yields.Equilibrium of 2a (R1=α-C10H7, R2= CH3) with hydrogen chloride and subsequent reaction with phenylmagnesium bromide followed by action of methyl- or butyllithium gave (S)-(-)-4a or (S)-(-)-4b with high enantiomeric excess, respectively.