期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 8, 页码 4639-4645出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01301
关键词
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资金
- Merck Research Laboratories New Technologies Review & Licensing Committee
- U.S. National Science Foundation [CHE-1464547, CHE-1764135]
The determination of the enantiopurity and the concentration of chiral compounds by chiroptical sensing with molecular probes is increasingly attractive for high-throughput screening applications including streamlined asymmetric reaction development. In this study, we use stereodynamic aluminum biphenolate complexes for quantitative ee and concentration analysis of amino alcohols and alpha-hydroxy acids. An important feature of the tropos biphenolate ligand used is the presence of a phenylacetylene antenna for optimal chirality recognition and CD/UV responses at high wavelengths. The complexation-driven chirality amplification yields strong CD signals, which allows quantitative chiroptical sensing with good accuracy. We show that aluminate biphenolate sensors can exhibit linear and nonlinear correlations between the induced CD signals and the enantiomeric composition or concentration of the chiral substrate.
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