Diastereoselective synthesis of quaternary alpha-amino acids from diketopiperazine templates

Stephen G. Davies, A. Christopher Garner, Jaqueline V. A. Ouzman, Paul M. Roberts, Andrew D. Smith, Emma J. Snow, James E. Thomson, Juan A. Tamayo, Richard J. Vickers

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2138-2147
Number of pages10
JournalOrganic & Biomolecular Chemistry
Volume5
Issue number13
DOIs
Publication statusPublished - 2007

Keywords

  • X-RAY-ANALYSIS
  • EFFICIENT ENANTIOSELECTIVE SYNTHESIS
  • CHIRAL NONRACEMIC ENOLATE
  • PHASE-TRANSFER CATALYSIS
  • ASYMMETRIC-SYNTHESIS
  • STEREOSELECTIVE-SYNTHESIS
  • 2,6-DIAMINOPIMELIC ACID
  • STEREOCONTROLLED SYNTHESIS
  • L-VALINE
  • IONIC LIQUIDS

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