3,5-dinitrobenzoylphenylglycine analogues bearing the 1,1′-binaphthalene moiety - Synthesis, conformational study, and application as chiral solvating agents

European Journal of Organic Chemistry

Volumn , Issue 11, 2001, Pages 2177-2184

  Iuliano, Anna ^a   Bartalucci, Debora ^a   Uccello Barretta, Gloria ^a   Balzano, Federica ^a   Salvadori, Piero ^a  

^a CNR   (Italy)

Author keywords

Chiral auxiliaries; Circular dichroism; NMR

Indexed keywords

2' HYDROXY 1,1' BINAPHTHYL 2 YL [(3,5 DINITROBENZOYL)AMINO](PHENYL)ACETATE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; DIASTEREOISOMER; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034988409     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200106)2001:11<2177::aid-ejoc2177>3.3.co;2-t     Document Type: Article

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41. It should be noted that 1b affords better results in terms of separation of the proton signals of 7 than (S)-2,2,2-trifluoro-1-(9-anthryl)ethanol, the most common CSA for amines, devoid of a carboxilic acid moiety. In fact, only the signal of the methine proton of 7b undergoes doubling in the presence of 3 equivalents of (S)-2,2,2-trifluoro-1-(9-anthryl)ethanol with a nonequivalence value of 17.8 Hz.