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 / Pagano, Angela; Marotta, Emanuela*; Mazzanti, Andrea; Petrillo, Giovanni; Tavani, Cinzia; Mancinelli, Michele. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 29:16(2018), pp. ST-2018-05-0307-C.2161-ST-2018-05-0307-C.2166. [10.1055/s-0037-1609908]
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
