A simple chiral derivatisation protocol for H-1 NMR spectroscopic analysis of the enantiopurity of O-silyl-1,2-amino alcohols

Magdalena E Powell, Andrew M Kelly, Steven D Bull, Tony D James

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A simple chiral derivatisation protocol for determining the enantiopurity of O-silyl-protected-1,2-amino alcohols by H-1 NMR spectroscopic analysis is described, which involves their treatment with 2-formylphenylboronic acid and enantiopure (syn)-methyl-2,3-dihydroxy-3-phenylpropionate to afford mixtures of imino-boronate esters whose diastereoisomeric ratio is an accurate reflection of the enantiopurity of the parent amino alcohol.
Original languageEnglish
Pages (from-to)876-879
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number8
DOIs
Publication statusPublished - Feb 2009

Keywords

  • 2-Amino alcohol
  • 1
  • Chiral derivatisation agent
  • H-1 NMR spectroscopy
  • Enantiomeric excess
  • Boronate esters

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