Chiral Phosphinites Derived from α-D-Glucofuranose and α-L-Idofuranose. A Comparison to Chiral Phosphines in Asymmetric Hydrogenation

Article abstract of DOI:10.1021/jo01289a013

Two chiral phosphinites and two chiral phosphines, which are derivatives of α-D-glucofuranose and α-L-idofuranose, were prepared and used as ligands in rhodium-catalyzed asymmetric hydrogenations.Six substrates were studied.Unlike phosphinites prepared from α-D-glucopyranose, the phosphinites prepared in this study were effective in inducing asymmetry in the hydrogenations of atropic acid and α-methylcinnamic acid.The phosphinites were frequently better chiral modifiers than phosphines when an acetamido group was not present in the substrate.