Highly enantioselective synthesis of (2S)-alpha-(hydroxymethyl)-glutamic acid by the catalytic Michael addition of 2-naphthalen-1-yl-2-oxazoline-4-carboxylic acid tert-butyl ester

Org Lett. 2005 Jul 21;7(15):3207-9. doi: 10.1021/ol050920s.

Abstract

[reaction: see text]. Highly enantioselective synthesis of a potent metabotropic receptor ligand, (2S)-alpha-(hydroxymethyl)-glutamic acid (2, HMG) was accomplished by the catalytic Michael addition of 2-naphthalen-1-yl-2-oxazoline-4-carboxylic acid tert-butyl ester (3b), using the phosphazene base, BEMP, in CH(2)Cl(2) at -60 degrees C in the presence of (S)-binaphthyl quaternary ammonium salt 4.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques*
  • Glutamates / chemical synthesis*
  • Ligands
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Oxazoles / chemistry*
  • Stereoisomerism

Substances

  • (hydroxymethyl)glutamic acid
  • 2-naphthalen-1-yl-2-oxazoline-4-carboxylic acid tert-butyl ester
  • Glutamates
  • Ligands
  • Naphthalenes
  • Oxazoles