Syntheses and Reactions of Optically Active Alkoxyaminosulfonium Salts

Abstract The optically active methoxymorpholino-p-tolylsulfonium salt has been synthesized by the reaction of optically active N-p-toluenesulfinylmorpholine with methyl trifluoromethanesulfonate. The sulfonium ion methylated benzylethylphenylamine and benzyl ethyl sulfide with asymmetric induction to give the optically active benzylethylmethylphenylammonium ion and benzylethylmethylsulfonium ion respectively. The optically active methoxymorpholino-p-tolylsulfonium salt and diaminosulfonium salts have been prepared in a one pot reaction between N-p-toluenesulfenyImorpholine and 1-chlorobenzotriazole with methanol in the presence of 1-menthol at −80 °C.