Using the same organocatalyst for asymmetric synthesis of both enantiomers of glutamic acid-derived Ni(II) complexes via 1,4-additions of achiral glycine and dehydroalanine Schiff base Ni(II) complexes

Amino Acids. 2012 Jul;43(1):299-308. doi: 10.1007/s00726-011-1076-y. Epub 2011 Sep 21.

Abstract

(S)- and (R)-BIMBOL were efficient PT catalysts of asymmetric Michael addition of prochiral Ni-PBP-Gly (1) to acrylic esters and malonic esters to Ni-PBP-Δ-Ala (2) correspondingly. The salient feature of the catalysis is opposite configurations of Glu prepared via the two paths with BIMBOL of the same configuration and a perspective novel catalytic procedure for the synthesis of Gla derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Carboxyglutamic Acid / chemistry
  • Alanine / analogs & derivatives
  • Alanine / chemistry
  • Catalysis
  • Glutamic Acid / chemistry*
  • Glycine / chemistry
  • Naphthols / chemistry*
  • Naphthols / metabolism
  • Nickel / chemistry
  • Schiff Bases / chemistry*
  • Stereoisomerism

Substances

  • Naphthols
  • Schiff Bases
  • Glutamic Acid
  • 1-Carboxyglutamic Acid
  • Nickel
  • dehydroalanine
  • Alanine
  • Glycine