Chiral guest recognition carbohydrates

Carbohydrates, Recognition of, p. 169 Carbonic Anhydrase Models, p. 178 Carcerands and Hernicarcerands. p. 189 Cation-n Interactions, p. 214 Cavitands, p. 219 Chiral Guest Recognition, p. 236 Classical Descriptions of Inclusion Compounds, p. 253 Classification and Nomenclature of Supramolecular Compounds, p. 261 Clathrate Hydrates, p. 274 Conzplexation of Fullerenes, p. 302 Concepts in Ciystal Engineering, p. 319 Crown Ethers, p. 326 Cryptands, p. 334 Cryptophanes, p. 340 Cyclodextrins, p. 398... 

An established area of application of macrocyclic polyethers is the stereoselective complexation of chiral guest primary alkylammonium salts by optically active host macrocycles. Full details of the resolution, optical stability, and inclusion into chiral hosts of the binaphthol (84), and also of the chiral recognition properties of crowns [e.g. (85)] based on simple carbohydrate precursors, have been reported this year. An extension of the latter work" utilizes derivatives of the more complex carbohydrates D-glucose and D-galactose. The macrobicyclic polyethers (86) derived from D-glycerol or pentaerythritol have been suggested as potential chiral (at the bridgeheads) cryptands. 

Two research groups have prepared chiral crown ethers based on carbohydrate units as the source of chirality. Stoddart et al have synthesized systems (57) and (58) (and some aza-analogues) from L-tartaric acid and o-mannitol respectively, and have observed chiral recognition in liquid-liquid extractions to the extent of 60 40 enantiomer ratios from racemates when the R-group is bulky (57a), (58a) and with a-phenylethylamine as guest. Similar results were obtained with the mixed binaphthyl-mannitol ligand (59). ... 

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