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Issue 8, 2019
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A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation

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Abstract

In this study, the first example of the carbene-catalyzed tandem dearomatization/rearomatization reaction of azonaphthalenes with α-chloroaldehydes is described. This protocol enables the efficient assembly of chiral dihydrocinnolinone derivatives in good yields with excellent enantioselectivities (up to 99% ee). Moreover, this strategy enables not only the highly enantioselective NHC-catalyzed nucleophilic aromatic substitution, but also a formal Csp2–Csp3 bond formation.

Graphical abstract: A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation

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Publication details

The article was received on 16 Oct 2018, accepted on 21 Dec 2018 and first published on 27 Dec 2018


Article type: Edge Article
DOI: 10.1039/C8SC04601H
Citation: Chem. Sci., 2019,10, 2501-2506
  • Open access: Creative Commons BY-NC license
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    A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation

    Z. Wu and J. Wang, Chem. Sci., 2019, 10, 2501
    DOI: 10.1039/C8SC04601H

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