Synthesis and elaboration of trans 2,3-diaryloxiranes

Abstract

2,3-Diaryloxiranes represent challenging intermediates for both their preparation and synthetic elaboration. Provided their synthesis in enantiopure form, they can be considered as suitable starting material for the synthesis of functionalized 1,2-diarylethanols, which are easily found in chiral auxiliaries, ligands and organocatalysts. The most efficient asymmetric methods for their preparation and synthetic elaboration are herein described. Regio- and stereoselective ring opening reactions, as reduction, nucleophilic opening with halides and oxygen nucleophiles have allowed straightforward access to versatile chiral intermediates such as aniline alcohols, halohydrins and 1,3-dioxolanes, their transformation affords chiral bases and bi- or tridentate ligands to use in asymmetric synthesis. ©ARKAT USA, Inc.