HIGHLY STEREOSELECTIVE FORMATION OF OPTICALLY PURE 2,4-OXAZOLIDINEDIONE VIA DIASTEREOSELECTIVE DIHYDROXYLATION OF (4S)-3((E)-3'-SUBSTITUTED-2'-PROPENOYL)-4-ISOPROPYL-2-OXAZOLIDINONE

Abstract

Catalytic asymmetric dihydroxylation (ADH) of (4S)-3-((E)-3'-substituted-2'-propenoyl)-4-isopropyl -2-oxazolidinone 1a and 1b resulted in the in situ rearrangement of the initially produced diols or its osmates to provide 3-((1'S)-1'-isopropyI-2'-hydroxyethyl)-5(S)-5((1'R)-1'-hydroxybenzyl (2a) and -hydroxyethyl (2b))-2,4-oxazolidinedione, respectively. The structure of 2a was determined by X-ray crystal structure analysis.