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Organocatalytic cycloaddition-elimination cascade for atroposelective construction of heterobiaryls.

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.

SUBMITTER: Xu WL

PROVIDER: S-EPMC8597853 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Organocatalytic cycloaddition-elimination cascade for atroposelective construction of heterobiaryls.

Xu Wen-Lei WL Zhao Wei-Ming WM Zhang Ru-Xia RX Chen Jie J Zhou Ling L

Chemical science 20211030 44

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 ...[more]

PMID: 34820108

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