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

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• 作者：Tomoya Fujiwara ; Masaru Segawa ; Hidehito Fujisawa ; Taiki Murai ; Tamiko Takahashi ; Kenji Omata ; Kuninobu Kabuto ; Siegfried N. Lodwig ; Clifford J. Unkefer ; Yoshio Takeuchi
• 关键词：Extraction ; Titanium ; Spectrophotometry ; Silicate rocks
• 刊名：Tetrahedron ; Asymmetry
• 出版年：2008
• 期刊代码：108_09574166
• 类别：ch
• 出版时间：17 April 2008
• 卷：19
• 期：7
• 页码：847-856
• 文件大小：388 K

摘要

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.