First access to the spin-labelled β-amino acid POAC in an enantiopure state by resolution through its binaphthyl esters

Karen Wright, Fernando Formaggio, Claudio Toniolo, Roland Török, Antal Péter, Michel Wakselman, Jean Paul Mazaleyrat

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Resolution of trans 3-(9-fluorenylmethyloxycarbonylamino)-1-oxyl-2,2,5,5- tetramethylpyrrolidine-4-carboxylic acid (Fmoc-POAC-OH) was quickly achieved upon esterification with (aR)-1,1′-binaphthyl-2,2′-diol, chromatographic separation of the obtained diastereomers, and facile saponification of the aryl ester function with removal of the chiral auxiliary.

Original languageEnglish
Pages (from-to)4183-4186
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number22
DOIs
Publication statusPublished - May 26 2003

Keywords

  • Binaphthol esters
  • Chiral nitroxides
  • Modified β-amino acids
  • POAC
  • Resolution
  • Spin-labelled amino acids

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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