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New Chiral Hosts Derived from Dimeric Tartaric Acid: Efficient Optical Resolution of Aliphatic Alcohols by Inclusion Complexation
Author(s) -
Tanaka Koichi,
Honke Shinji,
UrbanczykLipkowska Zofia,
Toda Fumio
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200009)2000:18<3171::aid-ejoc3171>3.0.co;2-t
Subject(s) - chemistry , tartaric acid , dimer , chiral resolution , inclusion compound , inclusion (mineral) , resolution (logic) , enantioselective synthesis , enantiomeric excess , cyanohydrin , organic chemistry , chirality (physics) , stereochemistry , enantiomer , combinatorial chemistry , molecule , catalysis , mineralogy , artificial intelligence , computer science , citric acid , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
The novel, chiral, host compounds 8 and 9 were derived from tartaric acid. Inclusion complexation with these host compounds permitted highly efficient resolution of some aliphatic alcohols ( 10 − 13 ). The symmetrical dimer host compound 8 is effective for optical resolution of alcohols 10 , 12 , and 13 by a combination of enantioselective inclusion complexation and distillation techniques. The unsymmetrical dimer host compound 9 is effective for optical resolution of cyanohydrin 11 . The crystal structures of the inclusion complexes were analyzed by X‐ray diffraction methods in order to elucidate the mechanism of the efficient chiral recognition in the inclusion crystals.