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Organocatalytic cycloaddition–elimination cascade for atroposelective construction of heterobiaryls† † Electronic supplementary information (ESI) available. CCDC 2101872 and 2101876. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/d1sc05161j

ABSTRACT: The first chiral phosphoric acid (CPA) catalyzed cycloaddition–elimination cascade reaction of 2-naphthol- and phenol-derived enecarbamates with azonaphthalenes has been established, providing a highly atroposelective route to an array of axially chiral aryl-C3-benzoindoles in excellent yields with excellent enantioselectivities. The success of this strategy derives from the stepwise process involving CPA-catalyzed asymmetric formal [3 + 2] cycloaddition and subsequent central-to-axial chirality conversion by elimination of a carbamate. In addition, the practicality of this reaction had been verified by varieties of transformations towards functionalized atropisomers. An organocatalytic asymmetric cycloaddition–elimination cascade reaction of aryl enecarbamates with azonaphthalenes has been developed to access axially chiral heterobiaryls in excellent yields and enantioselectivities.

SUBMITTER: Xu W

PROVIDER: S-EPMC8597853 | biostudies-literature |

REPOSITORIES: biostudies-literature

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