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

Chemical Science
Xiaoze BaoDamien Bonne

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.

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Citations

Mar 24, 2020·Angewandte Chemie·Xiaoze BaoDamien Bonne
Aug 6, 2020·Chemistry, an Asian Journal·Hui YangLing Zhou
Mar 30, 2021·Chemical Reviews·Jun Kee ChengBin Tan
Apr 29, 2021·Organic & Biomolecular Chemistry·Arianna BrandoleseAndrew D Smith
May 8, 2021·Journal of the American Chemical Society·Qianwen GaoQianghui Zhou
Jun 1, 2021·Accounts of Chemical Research·Tanno A Schmidt, Christof Sparr
Aug 29, 2020·Journal of the American Chemical Society·Omar M BelehScott J Miller

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Methods Mentioned

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