-Heterocyclic Carbene-Catalyzed [3 + 3] Annulation of Enals with Aminonaphthoquinones for the Synthesis of Functionalized Aza-anthraquinones.

J Org Chem

College of Chemistry and Materials Science, Chemical Biology Key Laboratory of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Hebei University, Baoding 071002, China.

Published: November 2024

Rapid construction of functionalized aza-anthraquinones has been successfully developed via NHC-catalyzed formal [3 + 3] annulation of 2-aminoquinones with enals. This reaction features several advantages, such as readily available starting materials, mild reaction conditions, and flexible product transformations. The study on the atroposelective version of this strategy was also carried out, and several C-N axial chiral aza-anthraquinones were synthesized in moderate yields with moderate to good enantioselectivities.

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http://dx.doi.org/10.1021/acs.joc.4c01655DOI Listing

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