Synthesis of enantiopure 1,3-oxazolidin-2-ones from α-dibenzylamino esters

Abstract

A new method to obtain enantiopure 5-substituted 1,3-oxazolidin-2-ones 1 from α-dibenzylamino esters 2 is reported. This methodology is based on the Lewis acid catalyzed stereoselective addition of trimethylsilyl cyanide to chiral α-dibenzylamino aldehydes 3. Magnesium chloride and zinc iodide were tested to catalyze the addition, obtaining higher stereoselectivity with zinc iodide than with magnesium chloride. ©ARKAT USA, Inc.