<i>N</i>-Heterocyclic Carbene-Catalyzed [3 + 3] Annulation of Enals with Aminonaphthoquinones for the Synthesis of Functionalized Aza-anthraquinones

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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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-11-04
DOI
https://doi.org/10.1021/acs.joc.4c01655
Citations
5
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
Field-Weighted Citation Impact
1.25

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article

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

A. V. Pan, Yubin Miao, Xiaoyong Duan, Jing Qi et al.
5 citations
The Journal of Organic Chemistry
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
1.25
article

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

A. V. Pan, Yubin Miao, Xiaoyong Duan, Jing Qi, Yanting Li
article en
5 citations

Abstract

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.

The Journal of Organic ChemistryVol. 89(22)
Hebei University (CN)
Natural Science Foundation of Hebei Province, Hebei University
Openalex Percentile: Top 22%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
1.25
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<i>N</i>-Heterocyclic Carbene-Catalyzed [3 + 3] Annulation of Enals with Aminonaphthoquinones for the Synthesis of Functionalized Aza-anthraquinones — A. V. Pan, Yubin Miao, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS