Stereospecific Synthesis of 2-Deuterio-3-hydroxybutanoate Esters. Regiochemistry and Stereochemistry of Homogenous Hydrogenation with Wilkinson's Catalyst

Article abstract of DOI:10.1021/jo00200a033

Hydrogenation of the methyl esters of (Z)- and (E)-3-(benzoyloxy)-2-butenoate produces reduced products in good yield with highly stereoselective syn additon.Reaction of the alkenes with deuterium is preferable to reaction of the 2-deuterioalkenes with hydrogen.NMR measurements indicated 99.8 percent or greater syn addition of D2 with the Z alkene.Addition of HD to the E alkene produced no regioselectivity, indicating that either the alkylrhodium intermediate forms without kinetic isotope effects or without regioselectivity.