Synthesis of (+)-polyoxamic acid and D-sorbitol from simple achiral allylic halides employing (S,S)-hydrobenzoin as a chiral source.

Coupling of cis-1-bromo-2-pentene and (S,S)-hydrobenzoin stannylene acetal followed by regio- and stereoselective transformations of the resulting allylic ether gave (+)-polyoxamic acid and a similar procedure was applied to the synthesis of D-sorbitol from trans-1-iodo-2-hexene.