STEREOSELECTIVE SYNTHESIS AND STEREOSPECIFIC ASYMMETRIC 1,2-REARRANGEMENTS OF CHIRAL SULFINYLCYCLOPROPANE DERIVATIVES

Stereoselective synthesis of chiral sulfinylcyclopropane derivatives and stereochemistry of the asymmetric 1,2-rearrangements are described. Heating of each stereoisomeric mesylate of (Ss)-1-(1-hydroxy-1-phenylethyl)-1-p-toluenesulfinylcyclopropane, followed by reduction of the sulfinyl group with acetyl chloride, provided (R)-(-)-4-methyl-4-phenyl-1-p-toluenesulfenylcyclobutene. In contrast, the same sequences of the stereoisomeric tosylates gave the corresponding enantiomeric sulfides stereospecifically with inversion of configuration. © 1990.