Enantioconvergent and Diastereoselective Three-Component Linear Reactions Enabled by Gold and Oxidative <i>N</i> -Heterocyclic Carbene Relay Catalysis

-heterocyclic carbenes (NHCs) for trimolecular reactions was disclosed. Racemic α-amino-ynones undergo facile conversion to racemic pyrrolin-3-ones under gold catalysis, which serve as potent nucleophilic C1 synthons, which engage easily available enals and phenols to generate linear products in moderate yields and excellent diastereo- and enantioselectivities under oxidative NHC catalysis. Synthetic utility of 2,2-disubstituted pyrrolinones is also demonstrated by facile conversion to pyrrolinone-fused γ-lactames in high yields.

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Publication Details

Journal
Organic Letters
Published
2026-04-12
DOI
https://doi.org/10.1021/acs.orglett.6c00952
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Enantioconvergent and Diastereoselective Three-Component Linear Reactions Enabled by Gold and Oxidative N -Heterocyclic Carbene Relay Catalysis

Zhifeng Tu, Zi‐Qiang Rong, Shifei Liu, Fei Xue et al.
Organic Letters
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
article

Enantioconvergent and Diastereoselective Three-Component Linear Reactions Enabled by Gold and Oxidative N -Heterocyclic Carbene Relay Catalysis

Zhifeng Tu, Zi‐Qiang Rong, Shifei Liu, Fei Xue, S Hücümenog ̆ lu, Hao An, Xia Wang
article en

Abstract

-heterocyclic carbenes (NHCs) for trimolecular reactions was disclosed. Racemic α-amino-ynones undergo facile conversion to racemic pyrrolin-3-ones under gold catalysis, which serve as potent nucleophilic C1 synthons, which engage easily available enals and phenols to generate linear products in moderate yields and excellent diastereo- and enantioselectivities under oxidative NHC catalysis. Synthetic utility of 2,2-disubstituted pyrrolinones is also demonstrated by facile conversion to pyrrolinone-fused γ-lactames in high yields.

Organic LettersVol. 28(16)
Ministry of Education of the People's Republic of China (CN), Huaibei Normal University (CN), Nanjing Forestry University (CN), Northwestern Polytechnical University (CN)
Huaibei Normal University
Openalex Percentile: Top 26%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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