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

Authors
Iuliano, A Bartalucci, D Uccello-Barretta, G Balzano, F Salvadori, P
Citation
A. Iuliano et al., 3,5-dinitrobenzoylphenylglycine analogues bearing the 1,1 '-binaphthalene moiety - Synthesis, conformational study, and application as chiral solvating agents, EUR J ORG C, (11), 2001, pp. 2177-2184
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
11
Year of publication
2001
Pages
2177 - 2184
Database
ISI
SICI code
1434-193X(200106):11<2177:3ABT1'>2.0.ZU;2-9
Abstract
The two new diastereoisomeric chiral auxiliaries (aR,R)-2'-Hydroxy-1,1' -bi naphthyl-2-yl [(3,5-dinitrobenzoyl)amino](phenyl)acetate and (aR,S)-2'-Hydr oxy-1,1'-binaphthyl-2-yl [(3,5-dinitrobenzoyl)amino](phenyl)acetate have be en synthesised and their efficiency as chiral solvating agents for the dete rmination of the enantiomeric composition of amides and amines has been dem onstrated. A conformational study of the two chiral solvating agents (CSAs) by means of NMR and CD spectroscopy is also presented.