Asymmetric [3 + 3] annulation of 3-hydroxyquinolin-2-ones <i>via</i> NHC organocatalysis

An efficient N-heterocyclic carbene (NHC)-catalyzed asymmetric C4-functionalization of quinolin-2-ones through a [3 + 3] annulation/ring-opening cascade reaction has been developed. This method employs 2-bromoenals and 3-hydroxyquinolin-2(1<i>H</i>)-ones to construct enantioenriched quinoline derivatives in moderate to good yields and with excellent enantioselectivity under mild conditions.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00848d
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
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article

Asymmetric [3 + 3] annulation of 3-hydroxyquinolin-2-ones via NHC organocatalysis

Weijun Yao, Zhen Wang, Heping Li
Organic & Biomolecular Chemistry
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
article

Asymmetric [3 + 3] annulation of 3-hydroxyquinolin-2-ones via NHC organocatalysis

Weijun Yao, Zhen Wang, Heping Li
article en

Abstract

An efficient N-heterocyclic carbene (NHC)-catalyzed asymmetric C4-functionalization of quinolin-2-ones through a [3 + 3] annulation/ring-opening cascade reaction has been developed. This method employs 2-bromoenals and 3-hydroxyquinolin-2(1<i>H</i>)-ones to construct enantioenriched quinoline derivatives in moderate to good yields and with excellent enantioselectivity under mild conditions.

Organic & Biomolecular ChemistryVol. 23(29)
Zhejiang Sci-Tech University (CN), Chongqing University (CN)
Clean water and sanitation
Openalex Percentile: Top 88%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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