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

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Abstract

We report the bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C–C stereogenic axes obtained by a two-fold 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.

Graphical abstract: Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C–C stereogenic axes

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Publication details

The article was received on 30 Aug 2019, accepted on 11 Nov 2019 and first published on 20 Nov 2019


Article type: Edge Article
DOI: 10.1039/C9SC04378K
Chem. Sci., 2020, Advance Article
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    Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C–C stereogenic axes

    X. Bao, J. Rodriguez and D. Bonne, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC04378K

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