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Issue 3, 2019
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Synthesis and characterization of novel chiral derivatizing agents containing β-keto-anthracene adducts (KAAs) by 1H-NMR: aromatic influence and chiral alcohol absolute configuration determination

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Abstract

New alternative chiral derivatizing agents, β-keto-anthracene adducts (KAAs), were accomplished and the influence of aromatic moieties at the α-carbon position for elucidation of the absolute configuration of chiral secondary alcohols via NMR was studied. The α-benzoyl substituted KAAs strongly enhance the anisotropic effect which produced greater ΔδRS values than other conventional reagents. We propose a simplified model to describe the conformations and to assign the absolute configuration in several chiral alcohol samples.

Graphical abstract: Synthesis and characterization of novel chiral derivatizing agents containing β-keto-anthracene adducts (KAAs) by 1H-NMR: aromatic influence and chiral alcohol absolute configuration determination

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Publication details

The article was received on 27 Oct 2018, accepted on 10 Dec 2018 and first published on 21 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02662A
Citation: Org. Biomol. Chem., 2019,17, 541-554

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    Synthesis and characterization of novel chiral derivatizing agents containing β-keto-anthracene adducts (KAAs) by 1H-NMR: aromatic influence and chiral alcohol absolute configuration determination

    N. Intakaew, P. Rithchumpon, C. Prommin, S. Yimklan, N. Kungwan, P. Thavornyutikarn and P. Meepowpan, Org. Biomol. Chem., 2019, 17, 541
    DOI: 10.1039/C8OB02662A

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