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Unmasking Inherent Chirality within the Cubane Skeleton
Author(s) -
Yoshino Nana,
Kato Yumi,
Shimada Yukako,
Williams Craig M.,
Matsubara Seijiro
Publication year - 2021
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.202100013
Subject(s) - chemistry , cubane , enantiomer , chirality (physics) , pharmacophore , ligand (biochemistry) , metalation , stereochemistry , halogenation , molecule , combinatorial chemistry , organic chemistry , receptor , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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.