C-2 Symmetric Synthesis of Bis(amino alcohol)oxalamides and Its Catalytic Activity


Cetin A.

ASIAN JOURNAL OF CHEMISTRY, vol.22, no.7, pp.5086-5092, 2010 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 22 Issue: 7
  • Publication Date: 2010
  • Journal Name: ASIAN JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5086-5092
  • Keywords: Enantioselectivity, Oxalamide, Catalytic, Diethyl zinc, ENANTIOSELECTIVE ADDITION, CHIRAL LIGANDS, ASYMMETRIC CATALYSIS, COMPLEX CATALYSTS, ALDEHYDES, DIETHYLZINC, BENZALDEHYDE, ZINC, DERIVATIVES, ALKYLATION
  • Van Yüzüncü Yıl University Affiliated: No

Abstract

The aim of this study is to evaluate C-2 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 C-2-symmetry were synthesized forming oxalic moiety main core. The catalytic effects of the N,N'-bis[(1R)-1-ethyl-2-hydroxyethyl]ethandiamide, N,N'-bis[(1S)-1-benzyl-2-hydroxyethyl]ethanediamide, N,N'-bis[(1S)-1-isobuty1-2-hydroxyethyl]ethanediamide and N,N'-bis[(1S)-1-isobutyl-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 C-2-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.