Regioselective addition of DDQ on a quinoid ring: an entry into chiral zwitterionic bridging ligands - Archive ouverte HAL
Journal Articles New Journal of Chemistry Year : 2018

Regioselective addition of DDQ on a quinoid ring: an entry into chiral zwitterionic bridging ligands

Abstract

The regioselective insertion of DDQ into a C-H bond of the 6π + 6π electron zwitterionic benzoquinonemonoimines 4a-c results in the formation of the novel chiral C-substituted quinoid ligands 11a-c. These Michael adducts feature a preserved zwitterionic form and a quaternary stereogenic carbon center as evidenced by the single crystal X-ray structure of the derivative 11a. The ECD spectra, optical rotations and racemization barriers of the two enantiomers of 11a were measured subsequently to their separation by a preparative chiral HPLC. Because the racemization of 11a is stopped in basic media, compounds 11a-c give a new entry in chiral zwitterionic bridging ligands.
Fichier principal
Vignette du fichier
NewJChem2018-PreprintForHal-AMU.pdf (1.26 Mo) Télécharger le fichier
Origin Files produced by the author(s)
Loading...

Dates and versions

hal-02460761 , version 1 (30-01-2020)

Identifiers

Cite

Gabriel Canard, Zhongrui Chen, Aprilliyani Suryaningtias, Marion Jean, Nicolas Vanthuyne, et al.. Regioselective addition of DDQ on a quinoid ring: an entry into chiral zwitterionic bridging ligands. New Journal of Chemistry, 2018, 42 (10), pp.8247-8252. ⟨10.1039/c7nj03765a⟩. ⟨hal-02460761⟩
34 View
137 Download

Altmetric

Share

More