Enantiomeric discrimination of α-hydroxy acids and N-Ts-α-amino acids by 1H NMR spectroscopy

被引：10

作者：

Gao, Guangpeng ^{[1
]}

Lv, Caixia ^{[1
]}

Li, Qiuju ^{[1
]}

Ai, Lin ^{[1
]}

Zhang, Jiaxin ^{[1
]}

机构：

[1] Beijing Normal Univ, Coll Chem, Beijing 100875, Peoples R China

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 48期

关键词：

Enantiomeric discrimination; alpha-Hydroxy acids and N-Ts-alpha-amino acids; H-1 NMR spectroscopy; CHIRAL SOLVATING AGENTS; CARBOXYLIC-ACIDS; ENANTIOSELECTIVE RECOGNITION; ABSOLUTE-CONFIGURATION; SHIFT-REAGENT; MANDELIC-ACID; CROWN MACROCYCLES; NMR DETERMINATION; BEARING; DERIVATIVES;

D O I：

10.1016/j.tetlet.2015.10.060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new kind of chiral compounds with multiple amino, amido and phenolic hydroxy groups has been synthesized from D-phenylalanine and D-phenylglycine, respectively. The enantiomeric discriminations of alpha-hydroxy acids and N-Ts-alpha-amino acids have been finished in the presence of the above chiral compounds as chiral solvating agents by H-1 NMR spectroscopy. The results show that the chiral compounds are highly effective and practical chiral solvating agents towards alpha-hydroxy acids and N-Ts-alpha-amino acids. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：6742 / 6746

页数：5

共 57 条

[1] Facile synthesis of (S,S)-1,2-diacylamides and (S,S)-1,2-diamines with C2-symmetry [J].

Ai, Lin ;

Xiao, Jichuan ;

Wang, Guo ;

Shen, Xiumin ;

Zhang, Cong .

SYNTHETIC COMMUNICATIONS, 2006, 36 (19) :2859-2875

[2] Ring-closing metathesis approach for the synthesis of optically active L-proline-based macrocycles [J].

Al-Azemi, Talal F. ;

Mohamod, Abdirahman A. ;

Vinodh, Mickey .

TETRAHEDRON, 2015, 71 (10) :1523-1528

[3] A Chiral Bisthiourea as a Chiral Solvating Agent for Carboxylic Acids in the Presence of DMAP [J].

Bian, Guangling ;

Fan, Hongjun ;

Yang, Shiwei ;

Yue, Huifeng ;

Huang, Huayin ;

Zong, Hua ;

Song, Ling .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18) :9137-9142

[4]

Bladon C., 2002, Pharmaceutical Chemistry: Therapeutic Aspects of Biomacromolecules

[5] Application of optically active aminonaphthols as NMR solvating agents for chiral discrimination of mandelic acid [J].

Chaudhary, Anju R. ;

Yadav, Priyanka ;

Bedekar, Ashutosh V. .

TETRAHEDRON-ASYMMETRY, 2014, 25 (09) :767-774

[6] Three-point versus two-point attachment of (R)- and (S)-amino acid methyl esters to a cobalt(III) chiroporphyrin:: Implications for the analysis of amino acid enantiomers by 1H NMR spectroscopy [J].

Claeys-Bruno, M ;

Toronto, D ;

Pécaut, J ;

Bardet, M ;

Marchon, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :11067-11068

[7] Enantio-differentiation of O-heterocycles using a binol-derived disulfonimide as a chiral solvating agent [J].

Couffin, A. ;

du Boullay, O. Thillaye ;

Vedrenne, M. ;

Navarro, C. ;

Martin-Vaca, B. ;

Bourissou, D. .

CHEMICAL COMMUNICATIONS, 2014, 50 (45) :5997-6000

[8] Structurally simple, modular amino alcohols for the recognition of carboxylic acids.: Application to the development of a new chiral solvating agent [J].

Cuevas, F ;

Ballester, P ;

Pericàs, MA .

ORGANIC LETTERS, 2005, 7 (24) :5485-5487

[9] Novel chiral Schiff base ligands from amino acid amides and salicylaldehyde [J].

Curini, M ;

Epifano, F ;

Maltese, F ;

Marcotullio, MC .

TETRAHEDRON LETTERS, 2002, 43 (21) :3821-3823

[10]

Dahiya R, 2007, PAK J PHARM SCI, V20, P317

← 1 2 3 4 5 6 →