78347-74-7

Upstream product

• 77382-91-3 (2S,4S)-3,4-dihydro-4-methyl-3-<(S)-1-α-naphthylethyl>-1,2,3-benzoxathiazine 2-oxide 
• 77383-02-9 2-{1-[(E)-(S)-1-Naphthalen-1-yl-ethylimino]-ethyl}-phenol 
• 90-02-8 salicylaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 7073-88-3 N-salicylidene-(S)-α-maphthylamine 
• 10420-89-0 (S)-1-(1-Naphthyl)ethylamine 
• 77382-90-2 (S)-o-<1-((S)-1-α-naphtylethylamino)ethyl>phenol 
• 77448-94-3 (2R,4S)-3,4-dihydro-4-methyl-3-<(S)-1-α-naphthylethyl>-1,2,3-benzoxathiazine 2-oxide 

Downstream Products

• 13153-10-1 (R)-(+)-butyl phenyl sulfoxide 
• 13153-10-1 (S)-(-)-n-butyl phenyl sulfoxide 

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

THE ACID-CATALYZED EPIMERIZATION AT THE SULFUR ATOM OF OPTICALLY ACTIVE 1,2,3-BENZOXATHIAZINE 2-OXIDE AND STEREOSPECIFICITY IN ITS NUCLEOPHILIC SUBSTITUTION

The acid-catalyzed epimerization of 2a was accomplished under extremely mild conditions by using hydrogen chloride, BF3*etherate, trifluoroacetic acid, acetic acid, and AlCl3 to give 2b.The action of nucleophiles to 2 proceeded highly stereospecifically with inversion of configuration.