The direct catalytic enantioselective synthesis of protected aryl β-hydroxy-α-amino acids

Michael C. Willis, Gary A. Cutting, Vincent J. D. Piccio, Matthew J. Durbin, Matthew P. John

Research output: Contribution to journalArticle

86 Citations (Scopus)

Abstract

The combination of three reagents-a tridentate pybox ligand (pybox = pyridine bis(oxazoline)), magnesium perchlorate, and Hunig base (iPr 2EtN)-allows the catalytic generation of a chiral glycine enolate from 1 that undergoes highly enantioselective addition to a range of aryl aldehydes 2. The protected aryl β-hydroxy-α-amino acid products obtained include a protected version of one of the aryl serine units present in the glycopeptide antibiotic vancomycin.
Original languageEnglish
Pages (from-to)1543-1545
Number of pages3
JournalAngewandte Chemie-International Edition
Volume44
Issue number10
DOIs
Publication statusPublished - 2005

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Glycopeptides
Vancomycin
Aldehydes
Glycine
Serine
Anti-Bacterial Agents
Ligands
Amino Acids
pyridine
magnesium perchlorate

Keywords

  • Synthesis (chemical)
  • Magnesium printing plates
  • Amino acids
  • Antibiotics
  • Aldehydes
  • Catalyst activity

Cite this

The direct catalytic enantioselective synthesis of protected aryl β-hydroxy-α-amino acids. / Willis, Michael C.; Cutting, Gary A.; Piccio, Vincent J. D.; Durbin, Matthew J.; John, Matthew P.

In: Angewandte Chemie-International Edition, Vol. 44, No. 10, 2005, p. 1543-1545.

Research output: Contribution to journalArticle

Willis, Michael C. ; Cutting, Gary A. ; Piccio, Vincent J. D. ; Durbin, Matthew J. ; John, Matthew P. / The direct catalytic enantioselective synthesis of protected aryl β-hydroxy-α-amino acids. In: Angewandte Chemie-International Edition. 2005 ; Vol. 44, No. 10. pp. 1543-1545.
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