Cyclic Sulfites,Key Intermediates in Synthesis of 1-Alkylamino-3-aryloxy-2-propanols from Glycidol

By treating glycidol with phenols a number of 3-aryloxypropanedioles were obtained. The latter with thionyl chloride afforded 4-aryloxymethyl-1,3,2-dioxathiolane 2-oxides. These compounds were also obtained from 4-chloromethyl-1,3,2-dioxathiolane 2-oxides by substitution aryloxy group for chlorine. The cyclic sulfides synthesized are universal intermediates in the synthesis of chiral aryloxypropanolamines among which are known -adrenoblockaders, cardiovascular drugs. From (S)-glycidol were synthesized (S)-alprenolol, (S)-propanolol, and (S)-thymolol.