Access to Atropisomerically Enriched Biaryls by the Coupling of Aryllithiums with Arynes under Control by Homochiral Oxazolines

Boubacar Yalcouye (1, 2) , Anaïs Brehier (1, 2) , David Augros (3) , Armen Panossian (3) , Sabine Choppin (3) , Matthieu Chessé , Francoise Colobert-Leuenberger (3) , Frédéric Leroux (3)

1 Substances naturelles/chimie moléculaire
2 LCM - Laboratoire de chimie moléculaire
3 LIMA - Laboratoire d'innovation moléculaire et applications

We report the preparation of axially stereoenriched biphenyls by the coupling of in situ generated aryllithiums and arynes using chiral oxazoline auxiliaries. The design of the aryne precursors, the choice of oxazoline and the reaction conditions were key to accessing the desired, highly substituted, atropisomerically enriched biarylic products. In one case, the two atropo-diastereomers could be obtained in isomerically pure form by column chromatographic separation and their absolute configurations established by X-ray crystallography. The stereoselectivity of the reaction seems to be governed by subtle parameters.

Domaines: Chimie organique

Boubacar Yalcouye, Anaïs Brehier, David Augros, Armen Panossian, Sabine Choppin, et al.. Access to Atropisomerically Enriched Biaryls by the Coupling of Aryllithiums with Arynes under Control by Homochiral Oxazolines. European Journal of Organic Chemistry, 2016, 2016 (4), pp.725-732. ⟨10.1002/ejoc.201501503⟩. ⟨hal-02304102⟩