Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C-C stereogenic axes - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Chemical Science Année : 2020

Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C-C stereogenic axes

Résumé

We report the bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal CC stereogenic axes obtained by a twofold central-to-axial chirality conversion upon oxidative aromatization. The key enantioenriched centrally chiral bis-dihydrobenzofuran precursors were synthesized via a bidirectional diastereo-and enantio-selective organocatalyzed domino reaction between simple achiral and easily accessible dihydroxylated aromatics and chloronitroalkenes. Moreover, the stereodivergent nature of the methodology was established by synthesizing both diastereomers of a non-symmetrically functionalized bis-axially chiral oligoarene.

Domaines

Chimie organique
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Dates et versions

hal-02436735 , version 1 (13-01-2020)

Identifiants

Citer

Xiaoze Bao, Jean Rodriguez, Damien Bonne. Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C-C stereogenic axes. Chemical Science, 2020, 11 (2), pp.403-408. ⟨10.1039/c9sc04378k⟩. ⟨hal-02436735⟩

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