A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylationElectronic supplementary information (ESI) available. CCDC 1858695. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc04601h

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 (...

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Main Authors: Wu, Zijun, Wang, Jian
Format: Article
Language:English
Online Access:Get full text
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Summary: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 Csp 2 -Csp 3 bond formation. In this study, the first example of carbene-catalyzed tandem dearomatization/rearomatization reaction of azonaphthalenes with α-chloroaldehydes is described.
ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc04601h