Planar Chiral Phosphoric Acids with Biphenylene-Tethered Paracyclophane Scaffolds: Synthesis, Characterization, and Catalytic Screening

Kevin Isaac (1) , Jérémy Stemper (1) , Vincent Servajean (1) , Pascal ́ Retailleau (1) , Julien Pastor (2) , Gilles Frison (2) , Karl Kaupmees (3) , Ivo Leito (3) , Jean-François Betzer (1) , Angela Marinetti (1)

1 ICSN - Institut de Chimie des Substances Naturelles
2 LCM - Laboratoire de chimie moléculaire
3 University of Tartu

Phosphoric acids with planar chiral paracyclophane scaffolds have been prepared in optically pure form starting from 1,8-dibromobiphenylene, by means of a chiral phosphorodiamidate as the phosphorylating agent. Structural characterization and configurational assignment have been performed by X-ray diffraction studies. The acids promote the organocatalytic enantioselective H-transfer reduction of α-arylquinolines with up to 90% enantiomeric excess.

Domains: Organic chemistry

Kevin Isaac, Jérémy Stemper, Vincent Servajean, Pascal ́ Retailleau, Julien Pastor, et al.. Planar Chiral Phosphoric Acids with Biphenylene-Tethered Paracyclophane Scaffolds: Synthesis, Characterization, and Catalytic Screening. Journal of Organic Chemistry, 2014, 79 (20), pp.9639-9646. ⟨10.1021/jo501769t⟩. ⟨hal-02152303⟩