Diastereoselective synthesis of quaternary alpha-amino acids from diketopiperazine templates

Org Biomol Chem. 2007 Jul 7;5(13):2138-47. doi: 10.1039/b704475e. Epub 2007 May 29.

Abstract

Sequential enolate alkylations of (S)-N(1)-methyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one and (S)-N(1)-p-methoxybenzyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (>90% de) affording quaternary alpha-amino acids in high enantiomeric excess (>98% ee) after deprotection and hydrolysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Crystallography, X-Ray
  • Diketopiperazines
  • Hydrolysis
  • Lactams / chemistry
  • Methylation
  • Models, Molecular
  • Molecular Structure
  • Piperazines / chemistry*
  • Protons
  • Stereoisomerism

Substances

  • Amino Acids
  • Diketopiperazines
  • Lactams
  • Piperazines
  • Protons