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

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.

SUBMITTER: Bao X

PROVIDER: S-EPMC7021203 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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

Bao Xiaoze X Rodriguez Jean J Bonne Damien D

Chemical science 20191120 2

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 <i>via</i> a bidirectional diastereo- and enantio-selective organocatalyzed domino reaction between simple achiral and easily accessible dihydroxylated aromatics and chloronitro ...[more]

PMID: 32153755

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