Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Conformational Analysis and Absolute Configuration of Axially Chiral 1-Aryl and 1,3-Bisaryl-xanthines

Conformational Analysis and Absolute Configuration of Axially Chiral 1-Aryl and 1,3-Bisaryl-xanthines
Sofia Perticarari, Andrea Mazzanti, Luca Prati, Michele Mancinelli
The xanthine scaffold is known to be the forefather of a class of biological active molecules. Xanthine is a planar framework in which an aryl substituent linked in the 1 or 3 position is driven out of the xanthine plane because of the steric hindrance exerted by the two carbonyls. This work analyses the stereodynamics of some 1-aryl and 1,3-bisaryl-xanthines and describes the steric requirements needed to produce stable heteroaromatic atropisomers or diastereoisomers, with one or two N–Csp2 stereogenic axes. The N–C racemization barrier was found to be bigger than 25 kcal/mol. The absolute configurations of the novel atropisomers has been assigned using TD-DFT simulation of ECD spectra.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01010

DOI: 10.1021/acs.joc.7b01010

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