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使用三氟甲基苯并咪唑基苯甲酸的¹⁹F核磁共振光谱法测定α-手性胺和仲醇的绝对构型

Application of F NMR Spectroscopy for Determining the Absolute Configuration of α-Chiral Amines and Secondary Alcohols Using Trifluoromethylbenzoimidazolylbenzoic Acid.

作者信息

Profous David, Kriegelstein Michal, Jurečka Petr, Cankař Petr

机构信息

Department of Organic Chemistry, Faculty of Science, Palacký University Olomouc, 17. listopadu 1192/12, Olomouc 779 00, Czech Republic.

Department of Physical Chemistry, Faculty of Science, Palacký University Olomouc, 17. listopadu 1192/12, Olomouc 779 00, Czech Republic.

出版信息

J Org Chem. 2025 Jul 18;90(28):9867-9884. doi: 10.1021/acs.joc.5c00879. Epub 2025 Jul 9.

DOI:10.1021/acs.joc.5c00879
PMID:40634259
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12281562/
Abstract

Axially chiral 2-(2-(trifluoromethyl)-1-benzo[]imidazol-1-yl)benzoic acid (TBBA) was employed as a chiral derivatizing agent for determining the absolute α-configuration of primary amines and secondary alcohols via F NMR spectroscopy. The method utilizes the trifluoromethyl group as a sensor, detecting the shielding effects induced by individual alcohol or amine substituents. This approach was tested on 46 alcohols and amines, demonstrating greater efficiency compared to the standard MTPA method.

摘要

轴向手性的2-(2-(三氟甲基)-1-苯并咪唑-1-基)苯甲酸(TBBA)被用作手性衍生试剂，通过氟核磁共振光谱法测定伯胺和仲醇的绝对α-构型。该方法利用三氟甲基作为传感器，检测单个醇或胺取代基引起的屏蔽效应。该方法在46种醇和胺上进行了测试，与标准的MTPA方法相比，显示出更高的效率。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/dabde869aef6/jo5c00879_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/e853212cc5cf/jo5c00879_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/1e4aa544b2f2/jo5c00879_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/bb052951345f/jo5c00879_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/9f9fafe0b302/jo5c00879_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/344e902bf6e7/jo5c00879_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/dabde869aef6/jo5c00879_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/e853212cc5cf/jo5c00879_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/1e4aa544b2f2/jo5c00879_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/bb052951345f/jo5c00879_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/9f9fafe0b302/jo5c00879_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/344e902bf6e7/jo5c00879_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0a6e/12281562/dabde869aef6/jo5c00879_0006.jpg

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Chiral Discrimination of Acyclic Secondary Amines by F NMR.
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