ENANTIOMERICALLY PURE BETA-AMINO SULFIDES AND BETA-AMINO THIOLS FROM EPHEDRINE

Ephedrine and pseudoephedrine are converted by means of a Mitsunobu reaction to respectively trans- and cis-aziridines, which can be ring-opened at the benzylic center with inversion of configuration by thiols and thiol acids. The trans-aziridine from ephedrine reacts also with H2S in acetone under which conditions the amino thiol is trapped as the thiazolane. The same aziridine also undergoes cycloaddition with CS2.