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A Supramolecular Chiral Auxiliary Approach: “Remote Control ”of Stereochemistry at a Hierarchically Assembled Dimeric Helicate

2016

Dimeric hierarchically-assembled titanium(IV) helicates are in solvent-dependent equilibrium with the corresponding monomers. Statistically formed mixtures of such complexes bearing chiral stereocontrolling ligands and achiral diene-substituted ligands show high diastereoselectivity and reasonable enantioselectivity in the Diels-Alder reaction with maleimides if the reaction proceeds with the dimer but not with the monomer. Thus, solvent dependent switching between the monomer and dimer enables on/off switching of the enantioselectivity.

Chiral auxiliary010405 organic chemistryChemistryDimerOrganic ChemistrySupramolecular chemistryNanotechnologyGeneral Chemistry010402 general chemistrychemistry01 natural sciencesCatalysis0104 chemical sciencesSolventchemistry.chemical_compoundCrystallographyMonomerSelf-assemblytitaniumta116dimeric helicateDiels–Alder reactionChemistry: A European Journal
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