Asymmetric Horner-Wadsworth-Emmons Reaction Utilizing Isomannide and Iso- sorbide Derivatives as Chiral Auxiliaries

Abstract

The diastereoselective Horner-Wadsworth-Emmons reaction of chiral phosphonates with s-symmetric 4-tert-butylcyclohexanone and 4phenylcyclohexanone was investigated by employing isomannide and isosorbide derivatives as chiral auxiliaries.a-Fluoro-a,b-unsaturated esters with an axis of chirality were obtained in diastereomer ratio up to 14 : 86 (aR : aS).