Cubane Chirality via Substitution of a “Hidden” Regular Tetrahedron
Nana Yoshino, Yumi Kato, Thibaud Mabit, Yuuya Nagata, Craig M. Williams, Mei Harada, Atsuya Muranaka, Masanobu Uchiyama, Seijiro Matsubara
Abstract
In the hexahedral hydrocarbon cubane, replacing hydrogen with other atoms at three positions within any one of the internal tetrahedrons can conceptually lead to the formation of a unique class of chiral molecules. In pursuit of this endeavor, we prepared 1,3-dibromo-4-deuteriocubane-N,N-diisopropylcarboxamide, which upon treatment with zincates affords 1,3,5-trisubstituted cubanes via simultaneous two-position substitution reactions. The proposed chiral attributes of this stereogeometric class were confirmed by enantiomeric resolution of a p-bromobenzyl derivative using chiral HPLC.
Topics & Concepts
CubaneChemistryTetrahedronEnantiomerSubstitution (logic)Chirality (physics)MoleculeDerivative (finance)StereochemistryCrystallographyComputational chemistryOrganic chemistryChiral symmetryEconomicsQuantum mechanicsProgramming languageNambu–Jona-Lasinio modelQuarkFinancial economicsComputer sciencePhysicsChemical Synthesis and AnalysisFluorine in Organic ChemistryAsymmetric Synthesis and Catalysis