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A Supramolecular Chiral Auxiliary Approach: “Remote Control” of Stereochemistry at a Hierarchically Assembled Dimeric Helicate
Author(s) -
Van Craen David,
Albrecht Markus,
Raabe Gerhard,
Pan Fangfang,
Rissanen Kari
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600158
Subject(s) - dimer , monomer , supramolecular chemistry , chemistry , solvent , titanium , stereochemistry , diene , combinatorial chemistry , polymer chemistry , polymer , crystallography , organic chemistry , crystal structure , natural rubber
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.