Unmasking Inherent Chirality within the Cubane Skeleton
Nana Yoshino, Yumi Kato, Yukako Shimada, Craig M. Williams, Seijiro Matsubara
Abstract
Abstract 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.
Topics & Concepts
ChemistryCubaneEnantiomerChirality (physics)PharmacophoreLigand (biochemistry)MetalationStereochemistryHalogenationMoleculeCombinatorial chemistryOrganic chemistryReceptorPhysicsBiochemistryQuantum mechanicsNambu–Jona-Lasinio modelQuarkChiral symmetry breakingAsymmetric Synthesis and CatalysisCoordination Chemistry and OrganometallicsSynthetic Organic Chemistry Methods