Synthesis, rapid resolution, and determination of absolute configuration of racemic 2,2'-binaphthyldiyl crown ethers and analogues via. beta. -cyclodextrin complexation

Journal Article · Fri Dec 27 00:00:00 EST 1985 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00350a025· OSTI ID:6036624

Armstrong, D W; Ward, T J; Czech, A; Czech, B P; Bartch, R A

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), Vol. 50:26
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
NAPHTHOLS
CHEMICAL PREPARATION
CONFIGURATION
POLYETHYLENE GLYCOLS
CHIRALITY
DEXTRIN
ENANTIOMORPHS
EXPERIMENTAL DATA
LIQUID COLUMN CHROMATOGRAPHY
RACEMATES
STEREOCHEMISTRY
ALCOHOLS
AROMATICS
CARBOHYDRATES
CHROMATOGRAPHY
DATA
GLYCOLS
HYDROXY COMPOUNDS
INFORMATION
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC POLYMERS
PARTICLE PROPERTIES
PHENOLS
POLYMERS
POLYSACCHARIDES
SACCHARIDES
SEPARATION PROCESSES
SYNTHESIS
400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)