Ternary ion-pair complexation: a protocol for chiral discrimination and the assignment of absolute configuration of chiral hydroxy acids

被引：25
作者：
Chaudhari, Sachin R. [1 ]
Suryaprakash, N. [1 ]
机构：
[1] Indian Inst Sci, Solid State & Struct Chem Unit, NMR Res Ctr, Bangalore 560012, Karnataka, India
来源：
NEW JOURNAL OF CHEMISTRY | 2013年 / 37卷 / 12期
关键词：
NUCLEAR-MAGNETIC-RESONANCE; OPTICALLY ACTIVE SOLVENTS; CARBOXYLIC-ACIDS; SOLVATING AGENTS; SHIFT-REAGENT; AMINO-ACIDS; NMR-SPECTROSCOPY; ENANTIOMERIC PURITY; DERIVATIZING AGENTS; STRUCTURALLY SIMPLE;
D O I：
10.1039/c3nj00779k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The study demonstrates the utility of ternary ion-pair complex formed among BINOL (1,1'-Bi-2-naphthol), a carboxylic acid and an organic base, such as, dimethylpyridine (DMAP), 1,4-diazabicyclo[2.2.2]octane (DABCO), as a versatile chiral solvating agent (CSA) for the enantiodiscrimination of carboxylic acids, measurement of enantiomeric excess (ee) and the assignment of absolute configuration of hydroxy acids. The proposed mechanism of ternary complex has wider application for testing the enantiopurity owing to the fact that the binary mixture using BINOL alone does not serve as a solvating agent for their discrimination. In addition, the developed protocol has an excellent utility for the assignment of the absolute configurations of hydroxy acids.
引用
收藏
页码：4025 / 4030
页数：6
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