Enantioselective and diastereoselective molecular recognition of neutral molecules

Molecular Tweezers as Synthetic Receptors: Molecular Recognition of Electron-Deficient Aromatic Substrates by Chemically Bonded Stationary Phases

“…[1] In addition to the relatively strong and, therefore, often dominating hydrogenbonding, [2] ion-pairing, [3] and hydrophobic forces, [4] arene Ϫarene interactions [5] are of particular importance for the formation of supermolecules. We recently reported that molecular tweezers 1 and 2 can act as synthetic receptors due to their ability to selectively bind electron-deficient aromatic and aliphatic compounds, as well as organic cations in solution.…”

Molecular Tweezers as Synthetic Receptors: Molecular Recognition of Electron-Deficient Aromatic and Aliphatic Substrates

“…[1] The study of such receptors should provide information about structure and stability of receptor ± substrate complexes and noncovalent interactions responsible for their formation. Besides the relatively strong and therefore often dominant hydrogen bonding, [2] ion pairing, [3] and the hydrophobic effect in aqueous media, [4] the arene ± arene interactions [5] are of particular importance for the formation of superstructures. As a result of many experimental and theoretical investigations, the attractive character of both CH ± p and p ± p interactions is commonly accepted.…”

Principles, Concepts and Strategies of Stereoselective Synthesis

“…A wide variety of discriminative interactions has been reported, among them anion recognition, [121][122][123] peptide and protein recognition, 124,125 carbohydrate recognition, 126 and recognition of carboxylic acids, 127 amino compounds, 128,129 and neutral molecules. 130 After the addition of a chiral lipophilic host or extractant confined in the organic phase, a host-mediated phase transfer of the substrate occurs. When the interaction of the chiral host with one enantiomer (e.g., (S)-enantiomer) is favored over the interaction with the opposite (R)-enantiomer, the organic phase then will be enriched with the (S)-enantiomer and the aqueous phase will be enriched with the (R)-enantiomer.…”