Planar Chiral Phosphoric Acids With Biphenylene-tethered Paracyclophane Scaffolds: Synthesis, Characterization, and Catalytic Screening

Abstract : 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.
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Submitted on : Thursday, October 2, 2014 - 2:23:12 PM
Last modification on : Thursday, June 20, 2019 - 10:14:01 AM

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Kévin 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, American Chemical Society, 2014, 79, pp.9639-9646. ⟨10.1021/jo501769t⟩. ⟨hal-01070825⟩

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