89423-49-4Relevant articles and documents
Studies on Chiral Organo-Sulfur Compounds. I. Asymmetric Synthesis of Sulfoxides with Optically Active o-Aminoalkylphenol Derivatives
Hiroi, Kunio,Sato, Shuko,Kitayama, Ryuichi
, p. 3471 - 3485 (2007/10/02)
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