Cubane, a hexahedral hydrocarbon, can be converted into an asymmetric molecule with a minimum of three substituents. The resulting chiral cubane can be used as a pharmacophore or a chiral ligand. Starting from the cubane carboxamide, the 1,2,3-substituted compound was synthesized by sequential ortho-metalation. The 1,3,5-substituted compound was synthesized by combining site-selective halogenation and halogen-metal exchange and the resulting racemate was subjected to enantiomeric resolution by HPLC.

中文翻译：

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揭示古巴骨架内的固有手性

古巴烷是一种六面体烃，可以转化为具有最少三个取代基的不对称分子。所得手性立方烷可用作药效团或手性配体。从立方甲酰胺开始，1,2,3-取代的化合物通过顺序邻位金属化合成。1,3,5-取代的化合物通过结合位点选择性卤化和卤素-金属交换合成，所得外消旋物通过HPLC进行对映体拆分。