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三氟甲基苯并咪唑基苯甲酸作为手性衍生化试剂用于确定β-手性氨基醇绝对构型的局限性。

Limitations of Trifluoromethylbenzoimidazolylbenzoic Acid as a Chiral Derivatizing Agent to Assign Absolute Configuration for β-Chiral Aminoalcohols.

作者信息

Kriegelstein Michal, Profous David, Přibylka Adam, Lyčka Antonín, Cankař Petr

机构信息

Department of Organic Chemistry, Faculty of Science, Palacký University, 17. Listopadu 12, 771 46 Olomouc, Czech Republic.

Faculty of Science, University of Hradec Králové, Rokitanského 62, CZ-500 03 Hradec Králové 3, Czech Republic.

出版信息

ACS Omega. 2022 Apr 4;7(15):12734-12746. doi: 10.1021/acsomega.1c07234. eCollection 2022 Apr 19.

DOI:10.1021/acsomega.1c07234
PMID:35474810
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9025982/
Abstract

Axially chiral 2-(2-(trifluoromethyl)-1-benzo[]imidazole-1-yl)benzoic acid (TBBA) was used as a chiral derivatizing agent to evaluate the limits of absolute configuration assignment for β-chiral aminoalcohols. Seven Boc-aminoalcohols and eight variously -substituted ()-phenylglycinols were prepared, and their TBBA esters were analyzed by NMR spectroscopy. Diverse substitution at the β-position was employed to demonstrate the effect of structure on the general conformational model and reliability of the absolute configuration assignment. It was concluded that hydrogen bond formation and steric hindrance were the main factors affecting the correct assignment for Boc-aminoalcohols.

摘要

轴向手性的2-(2-(三氟甲基)-1-苯并咪唑-1-基)苯甲酸(TBBA)被用作手性衍生化试剂，以评估β-手性氨基醇绝对构型归属的局限性。制备了七种叔丁氧羰基氨基醇和八种不同取代的()-苯基甘醇，并通过核磁共振光谱对它们的TBBA酯进行了分析。在β位进行不同的取代，以证明结构对一般构象模型和绝对构型归属可靠性的影响。得出结论，氢键形成和空间位阻是影响叔丁氧羰基氨基醇正确归属的主要因素。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/2248c7106b88/ao1c07234_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/1e74bf49adce/ao1c07234_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/d3a111619e85/ao1c07234_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/4f252da07206/ao1c07234_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/3043f0d011ca/ao1c07234_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/2248c7106b88/ao1c07234_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/1e74bf49adce/ao1c07234_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/d3a111619e85/ao1c07234_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/4f252da07206/ao1c07234_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/3043f0d011ca/ao1c07234_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f98/9025982/2248c7106b88/ao1c07234_0006.jpg

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