Abstract
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-{1-((S)-1-α-naphthylethylamino)ethyl} phenol, was found to be the most efficient and recyclable chiral source for the asymmetric synthesis of sulfoxides.
