N,N-Dialkylhydrazones as Versatile Umpolung Reagents in Enantioselective Anion-Binding Catalysis.

ABSTRACT: An enantioselective anion-binding organocatalytic approach with versatile N,N-dialkylhydrazones (DAHs) as polarity-reversed (umpolung) nucleophiles is presented. For the application of this concept, a highly ordered hydrogen-bond (HB) network between a carefully selected CF₃ -substituted triazole-based multidentate HB-donor catalyst, the ionic substrate and the hydrazone in a supramolecular chiral ion-pair complex was envisioned. The formation of such a network was further supported by both experimental and computational studies, which showed the crucial role of the anion as a template unit. The asymmetric Reissert-type reaction of quinolines as a model test reaction chemoselectively delivered highly enantiomerically enriched hydrazones (up 95:5 e.r.) that could be further deriv

SUBMITTER: Gomez-Martinez M 

PROVIDER: S-EPMC7986925 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature