Synthesis, rapid resolution, and determination of absolute configuration of racemic 2,2'-binaphthyldiyl crown ethers and analogues via. beta. -cyclodextrin complexation
Journal Article
·
· J. Org. Chem.; (United States)
Twenty racemic and four diastereomeric 2,2'-binaphthyldiyl crown ethers and analogues were synthesized. Chiral interactions between these compounds and immobilized ..beta..-cyclodextrin were examined. Thirteen of the enantiometic pairs and two of the diastereomers were successfully resolved. It was found that relatively small changes in the structure of these compounds could have large effects on chiral recognition. In general, the (-)-S enantiomers formed stronger inclusion complexes with ..beta..-cyclodextrin than did the (+)-R enantiomers. 40 references, 2 figures, 2 tables.
- Research Organization:
- Texas Tech Univ., Lubbock
- DOE Contract Number:
- AS05-84ER13159
- OSTI ID:
- 6036624
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 50:26; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALCOHOLS
AROMATICS
CARBOHYDRATES
CHEMICAL PREPARATION
CHIRALITY
CHROMATOGRAPHY
CONFIGURATION
DATA
DEXTRIN
ENANTIOMORPHS
EXPERIMENTAL DATA
GLYCOLS
HYDROXY COMPOUNDS
INFORMATION
LIQUID COLUMN CHROMATOGRAPHY
NAPHTHOLS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC POLYMERS
PARTICLE PROPERTIES
PHENOLS
POLYETHYLENE GLYCOLS
POLYMERS
POLYSACCHARIDES
RACEMATES
SACCHARIDES
SEPARATION PROCESSES
STEREOCHEMISTRY
SYNTHESIS
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALCOHOLS
AROMATICS
CARBOHYDRATES
CHEMICAL PREPARATION
CHIRALITY
CHROMATOGRAPHY
CONFIGURATION
DATA
DEXTRIN
ENANTIOMORPHS
EXPERIMENTAL DATA
GLYCOLS
HYDROXY COMPOUNDS
INFORMATION
LIQUID COLUMN CHROMATOGRAPHY
NAPHTHOLS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC POLYMERS
PARTICLE PROPERTIES
PHENOLS
POLYETHYLENE GLYCOLS
POLYMERS
POLYSACCHARIDES
RACEMATES
SACCHARIDES
SEPARATION PROCESSES
STEREOCHEMISTRY
SYNTHESIS