(S)-alpha-methyl,alpha-amino acids: a new stereocontrolled synthesis

Amino Acids. 2010 Mar;38(3):829-37. doi: 10.1007/s00726-009-0289-9. Epub 2009 Apr 12.

Abstract

A new and convenient stereocontrolled synthesis of the optically pure (S)-alpha-methyl,alpha-amino acids 6(a-d) that exploits the chiral synthon 1,4-N,N-[(S)-1-phenylethyl]-piperazine-2,5-dione (1) is described. The (S)-1-phenylethyl group, bonded to each of the N-atoms of the 2,5-diketopiperazine, acts as a chiral inductor in the first alkylation, while the steric hindrance appears to be the determining factor of stereocontrol in third and forth alkylation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / analogs & derivatives
  • Alanine / chemical synthesis
  • Alanine / chemistry
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • Aminobutyrates / chemical synthesis
  • Aminobutyrates / chemistry
  • Crystallography, X-Ray
  • Diketopiperazines / chemical synthesis
  • Diketopiperazines / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism
  • Valine / chemical synthesis
  • Valine / chemistry

Substances

  • 1,4-N,N-(phenylethyl)piperazine-2,5-dione
  • Amino Acids
  • Aminobutyrates
  • Diketopiperazines
  • isovaline
  • 2-amino-4-phenylbutyric acid
  • Valine
  • Alanine