A series of atropisomeric molecules containing the indole ring and two stereogenic axes were prepared. The four atropisomers were resolved by enantioselective HPLC. The rotational barriers of the indole-naphthyl axes were evaluated by means of kinetic analysis either by NMR or enantioselective HPLC. The absolute configuration of the 'atropisomers was determined by a combination of X-ray spectroscopy and TD-DFT simulation of electronic circular dichroism spectra.

Stereodynamic Analysis of New Atropisomeric 4,7-Di(naphthalen-1-yl)-5,6-dinitro-1 H -indoles

Marotta, Emanuela;Mazzanti, Andrea;Mancinelli, Michele
2018

Abstract

A series of atropisomeric molecules containing the indole ring and two stereogenic axes were prepared. The four atropisomers were resolved by enantioselective HPLC. The rotational barriers of the indole-naphthyl axes were evaluated by means of kinetic analysis either by NMR or enantioselective HPLC. The absolute configuration of the 'atropisomers was determined by a combination of X-ray spectroscopy and TD-DFT simulation of electronic circular dichroism spectra.
Pagano, Angela; Marotta, Emanuela*; Mazzanti, Andrea; Petrillo, Giovanni; Tavani, Cinzia; Mancinelli, Michele
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/657779
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