C2 Symmetric Synthesis of Bis(amino alcohol)oxalamides and Its Catalytic Activity

Abstract

The aim of this study is to evaluate C₂ symmetric synthesis of bis(amino alcohol)oxalamides and the catalytic activity diethyl zinc to benzaldehyde. Syntheses of diamidediols were achieved nearly quantitatively by reacting oxalic acids methyl esters with amino alcohols directly in a single step reactions and mild conditions. Four modular and rigid diamidediols having C₂- symmetry were synthesized forming oxalic moiety main core. The catalytic effects of the N,N'- bis[(1R)-1-ethyl-2-hydroxyethyl]ethanediamide, N,N'-bis[(1S)-1-benzyl-2-hydroxyethyl]- ethanediamide, N,N'-bis[(1S)-1-isobutyl-2-hydroxyethyl]ethanediamide and N,N'-bis[(1S)-1- secbutyl-2-hydroxyethyl]ethanediamide were tested and also N,N'-bis[(1S)-1-benzyl-2- hydroxyethyl]ethanediamide, N,N'-bis[(1S)-1-isobutyl-2-hydroxyethyl]ethanediamide were synthesized. The catalytic activity of C₂-symmetric diamidediols on the addition reaction of diethyl zinc to benzaldehyde and effects of alkyl moiety bonded to stereogenic center on enantioselectivity were conducted out.