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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.

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Publication details

The article was received on 03 Oct 2017, accepted on 12 Feb 2018 and first published on 12 Feb 2018


Article type: Paper
DOI: 10.1039/C7NJ03765A
Citation: New J. Chem., 2018, Accepted Manuscript
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    Regioselective addition of DDQ on a quinoid ring: an entry into chiral zwitterionic bridging ligands

    G. Canard, Z. Chen, A. Suryaningtias, M. Jean, N. Vanthuyne, M. Giorgi, C. Roussel and O. Siri, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C7NJ03765A

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