Systematic Design of Chiral Molecules of High Symmetry. Achiral Skeletons Substituted with Chiral Ligands.

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  • Fujita Shinsaku
    Department of Chemistry and Materials Technology, Kyoto Institute of Technology

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For the design of chiral molecules of high symmetry, a set of substitution positions in an achiral skeleton of G-symmetry are replaced by chiral ligands or proligands of the same kind so that there emerge three criteria of generating chiral molecules or promolecules. Thus, Criterion 1 controls the desymmetrization of a homospheric orbit in an achiral skeleton, where the resulting molecule or promolecule is determined to belong to the maximum chiral subgroup of G in agreement with a size-invariant subduction. Criterion 2 for the desymmetrization of an enantiospheric orbit shows that the resulting molecule or promolecule is determined to belong to the maximum chiral subgroup of G and that the original enantiospheric orbits are divided into two hemispheric orbits of equal size. Criterion 3 deals with a chiral skeleton, where subsitution by chiral ligands or proligands of the same kind is examined as the transformation of the hemispheric orbit in the skeleton. Although no change of symmetry occurs from a group-theoretical point of view, the transformation is shown to be important chemically, since relevant ligands or proligands alter the stereochemical properties.

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