Reliable assignment of absolute configuration of chiral amines based on the analysis of 1H NMR spectra of their CFTA amide diastereomers

Tomoya Fujiwara, Masaru Segawa, Hidehito Fujisawa, Taiki Murai, Tamiko Takahashi, Kenji Omata, Kuninobu Kabuto, Siegfried N. Lodwig, Clifford J. Unkefer, Yoshio Takeuchi

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Applications of the CFTA method, a new and reliable procedure for the determination of the absolute configuration of chiral primary amines, are described in detail. In addition to the very high reactivity of CFTA chloride, the stable anti-periplanar conformers of CFTA amides, associated with the chiral structure of fluorine atom on a stereogenic center, are the key factors that make the technique of using 1H NMR analysis of the CFTA diastereomers very reliable. In particular, this method is useful for the determination of the absolute stereochemistry of isotopically multi-labeled amino acid derivatives.

Original languageEnglish
Pages (from-to)847-856
Number of pages10
JournalTetrahedron Asymmetry
Volume19
Issue number7
DOIs
Publication statusPublished - 2008 Apr 17

ASJC Scopus subject areas

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

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