[2.2]Paracyclophane-Derived Planar-Chiral Hydrogen-Bond Receptors

[2.2]Paracyclophane-Derived Planar-Chiral Hydrogen-Bond Receptors
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[2.2]对环芳烷衍生的平面手性氢键受体

DOI:
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发表时间:
2012
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影响因子:
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通讯作者:
J. Paradies
J. Paradies
中科院分区:
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文献类型:
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作者:
Jakob F. Schneider;R. Fröhlich;J. Paradies

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讨论了以[2.2]对环磷酸盐为骨架的平面手性氢键给电子体的发展。简要综述了获得功能化对映体[2.2]对环番衍生物的一般策略,重点介绍了合成平面手性硫脲衍生物的适宜前驱体。本文报道了十四个氢键给体的合成。用~1H 核磁共振波谱和X-射线结晶学研究了四种硫脲衍生物与氢键受体(二甲亚砜和四甲基氯化铵)的相互作用。一系列手性对映体被应用于不对称氢键催化。
The development of planar-chiral hydrogen-bond donors based on the [2.2]paracyclophane scaffold is discussed. General strategies to access functionalized enantiopure [2.2]paracyclophane derivatives are briefly reviewed, with the focus on suitable precursors for the synthesis of planar-chiral thiourea derivatives. The synthesis of fourteen hydrogen-bond donors is described. The interaction of four thiourea derivatives with hydrogen-bond acceptors (DMSO and tetramethylammonium chloride) was investigated by 1H NMR spectroscopy and X-ray crystallography. A selection of enantiomerically pure planar-chiral derivatives was applied in asymmetric hydrogen-bond catalysis.
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