Related Experiment Video
Updated: Mar 26, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
A Supramolecular Chiral Auxiliary Approach: "Remote Control" of Stereochemistry at a Hierarchically Assembled Dimeric
David Van Craen1, Markus Albrecht2, Gerhard Raabe1
1Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074, Aachen, Germany.
Abstract:
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.
Related Concept Videos
Prochirality
Molecules with Multiple Chiral Centers
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:
Chirality in Nature

