Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates

Crown ethers: sensors for ions and molecular scaffolds for materials and biological models.

The Design of Molecular Hosts, Guests, and Their Complexes (Nobel Lecture)†

1,1‘-Binaphthyl Dimers, Oligomers, and Polymers: Molecular Recognition, Asymmetric Catalysis, and New Materials†

Enantiomeric Recognition of Amine Compounds by Chiral Macrocyclic Receptors.

Host-guest complexation. 8. Macrocyclic polyethers shaped by two rigid substituted dinaphthyl or ditetralyl units

Host molecules have been designed and synthesized to selectively complex and lipophilize guest molecules. Examples of the use of the following binding interactions are given: hydrogen bonding, ion pairing, cation to n-electrons, carbonyl to n-electrons and pi-pi bonding. Multiheteromacrocycles have been prepared whose association constants with tert -butylammonium salts in chloroform range from 6 M -1 . Host molecules with built-in counterions have been prepared that selectively complex and lipophilize metal and alkylammonium cations. Locations of complementary binding sites and non-complementary steric barriers provide for selective binding by host molecules of candidate guest molecules. Locations of appropriate chiral barriers and multiple complexing sites in guest compounds have led to the complete optical resolution of host compounds by optically active amino acids, and of amino acid esters by optically active host compounds. Ratios of association constants for diastereomeric complexes in excess of ten have been obtained. A molecular basis for designing an amino acid resolving machine has been developed.

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Chiral recognition in complexation of guests by designed host molecules

Host-guest complexation. 13. High chiral recognition of amino esters by dilocular hosts containing extended steric barriers

Reduktion das Alkylderivat (II) erhalten, das uber das Cinchoninsalz des Phosphorsaurediesters von (II) in seine optischen Antipoden gespalten wird.

Models for chiral recognition in molecular complexation

Chiral cyclic polyether hosts containing one 2,2′-substituted-1,1′-binaphthyl and one 2,2′-substituted-3,3′-dimethyl-1,1′-binaphthyl units in CDCl3–CD3CN or CDCl3 have been used to extract from water differentially by factors of up to 52 the enantiomers of eight amino-acids and five amino-ester salts.

Stephen C. Peacock

Papers

Host-guest complexation. 8. Macrocyclic polyethers shaped by two rigid substituted dinaphthyl or ditetralyl units

Chiral recognition in complexation of guests by designed host molecules

Host-guest complexation. 13. High chiral recognition of amino esters by dilocular hosts containing extended steric barriers

Models for chiral recognition in molecular complexation

High chiral recognition in α-amino-acid and -ester complexation