Unmasking Inherent Chirality within the Cubane Skeleton

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...

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Bibliographic Details
Published in:Israel journal of chemistry 2021-07, Vol.61 (7-8), p.380-386
Main Authors: Yoshino, Nana, Kato, Yumi, Shimada, Yukako, Williams, Craig M., Matsubara, Seijiro
Format: Article
Language:English
Subjects:
Charge-shifted bond
Chiral Cubane
Chirality
Cubane
Metalation
Organozincate
Substitutes
Synthesis
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Summary: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.
ISSN:0021-2148
1869-5868
DOI:10.1002/ijch.202100013