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Reliable assignment of absolute configuration of chiral amines based on the analysis of1H NMR spectra of their CFTA amide diastereomers

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
19
Issue
7
Identifiers
DOI: 10.1016/j.tetasy.2008.03.003
Disciplines
  • Chemistry

Abstract

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.

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