Observing the enantiomeric 1H chemical shift non-equivalence of several α-amino ester signals using tris[3- (trifluoromethylhydroxymethylene)-(+)-camphorato]samarium(III): A chiral lanthanide shift reagent that causes minimal line broadening

Kenji Omata, Susumu Aoyagi, Kuninobu Kabuto

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

The chiral lanthanide shift reagent, tris[3- (trifluoromethylhydroxymethylene)-(+)-camphorato]samarium(III) [Sm(tfc) 3], was shown to resolve the 1H NMR signals of the enantiomers of α-amino esters without causing serious line broadening. This distinctive feature of Sm(tfc) 3 made it possible to examine the enantiomeric chemical shift non-equivalence of several protons in ester substrates, increasing the reliability of the empirical assignment of the absolute configuration as compared to earlier techniques.

Original languageEnglish
Pages (from-to)2351-2356
Number of pages6
JournalTetrahedron Asymmetry
Volume15
Issue number15
DOIs
Publication statusPublished - 2004 Aug 9

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint Dive into the research topics of 'Observing the enantiomeric <sup>1</sup>H chemical shift non-equivalence of several α-amino ester signals using tris[3- (trifluoromethylhydroxymethylene)-(+)-camphorato]samarium(III): A chiral lanthanide shift reagent that causes minimal line broadening'. Together they form a unique fingerprint.

  • Cite this