Efficient Synthesis of Chiral Binaphthol Aldehyde with Phenyl Ether Linkage for Enantioselective Extraction of Amino Acids

被引：4

作者：

Choi, Misun ^{[1
]}

Jun, Moo-Jin ^{[2
]}

Kim, Kwan Mook ^{[1
]}

机构：

[1] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 120750, South Korea

[2] Korea Inst Sci & Technol Informat, ReSEAT Program, Seoul 130741, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2015年 / 36卷 / 07期

基金：

新加坡国家研究基金会;

关键词：

Enantioselective extractor; Optical resolution; Chiral imine; LIQUID-LIQUID-EXTRACTION; HOST-GUEST COMPLEXATION; ASYMMETRIC-SYNTHESIS; RECOGNITION; SEPARATION; RESOLUTION; TRANSPORT;

D O I：

10.1002/bkcs.10354

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A binaphthol aldehyde with phenyl ether linkage, compound 2, has been synthesized starting from binaphthol-3-carboxylic acid. The axially chiral binaphthol ring was racemized during the synthesis due to high temperatures required in O-phenylation reaction. The enantiomerically pure form of 2 was obtained from the resolution of the diastereomeric imine of 2. Optically pure compound (S)-2 was applied to the enantioselective liquid-liquid extraction of amino acid between CH2Cl2 and aqueous layers. The stereoselectivities, that is, d/l ratio of the amino acid extracted, ranged from 3.57 to 11.1. One carbon was absent in compound (S)-2 compared to the compound (S)-1 with benzyl ether linkage, which differentiated the conformations of their imines formed with amino acids.

引用

页码：1834 / 1837

页数：4

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