Rapid determination of enantiomeric excess of α-chiral aldehydes using circular dichroism spectroscopy

被引：11

作者：

Barman, Sanmitra ^{[1
]}

Anslyn, Eric V. ^{[2
]}

机构：

[1] Univ Texas Austin, Austin, TX 78712 USA

[2] Univ Texas Austin, Dept Chem, Austin, TX 78746 USA

来源：

TETRAHEDRON | 2014年 / 70卷 / 06期

关键词：

Enantiomeric excess; Exciton coupled circular dichroism; High-throughput screening; Metal to ligand charge transfer; INDICATOR DISPLACEMENT ASSAYS; TANDEM ENZYME ASSAYS; CARBOXYLIC-ACIDS; ENANTIOSELECTIVE CATALYSTS; AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; PARALLEL SYNTHESIS; ABSOLUTE-CONFIGURATION; NMR-SPECTROSCOPY; SHIFT-REAGENT;

D O I：

10.1016/j.tet.2013.11.086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for enantiodiscrimination of alpha-chiral aldehydes is reported. The method utilizes circular dichroism (CD) spectroscopy and a sensing ensemble composed of 2-(1-methylhydrazinyl) pyridine (1) and Fe(II)(TfO)(2). Aldehydes react rapidly with hydrazine (1) to form chiral imines, which form complexes with Fe(II). By monitoring the CD bands above 320 nm, one can determine the enantiomeric excess (ee) values of a-chiral aldehydes with an average absolute error of +/- 5%. The analysis was fast, and thus can have potential applications in high-throughput screening (HTS) of catalytic asymmetric induction. (C) 2013 Elsevier Ltd. All rights reserved.

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收藏

页码：1357 / 1362

页数：6

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