Enantio- and diastereoselective cyclopropanation of CF3-imidoyl sulfoxonium ylides by chiral-at-metal Rh(III) complex

An enantio- and diastereoselective cyclopropanation of CF 3 -imidoyl sulfoxonium ylides with α,β-unsaturated 2-acyl imidazoles catalyzed by chiral-at-metal Rh(III) complex has been demonstrated for the first time. This work provides a practical approach for assembling 1,2,3-trisubstituted chiral cyclopropane with CF 3 -imidoyl structural units under mild reaction conditions, which has the advantages including broad substrates and good functional tolerance. In addition, a scale-up experiment and the synthetic transformations of the cycloadducts further highlight the synthetic utility. An enantio- and diastereoselective cyclopropanation of CF 3 -imidoyl sulfoxonium ylides with α,β-unsaturated 2-acyl imidazoles catalyzed by chiral-at-metal Rh(III) complex has been demonstrated for the first time. This work provides a practical approach for assembling 1,2,3-trisubstituted chiral cyclopropane with CF 3 -imidoyl structural units under mild reaction conditions, which has the advantages including broad substrates and good functional tolerance.

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Publication Details

Journal
Green Synthesis and Catalysis
Published
2025-09-01
DOI
https://doi.org/10.1016/j.gresc.2025.08.006
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
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article

Enantio- and diastereoselective cyclopropanation of CF3-imidoyl sulfoxonium ylides by chiral-at-metal Rh(III) complex

Jixin Pian, Shiwu Li, Zhifei Zhao
Green Synthesis and Catalysis
Cyclopropane Reaction Mechanisms
article

Enantio- and diastereoselective cyclopropanation of CF3-imidoyl sulfoxonium ylides by chiral-at-metal Rh(III) complex

Jixin Pian, Shiwu Li, Zhifei Zhao
article en

Abstract

An enantio- and diastereoselective cyclopropanation of CF 3 -imidoyl sulfoxonium ylides with α,β-unsaturated 2-acyl imidazoles catalyzed by chiral-at-metal Rh(III) complex has been demonstrated for the first time. This work provides a practical approach for assembling 1,2,3-trisubstituted chiral cyclopropane with CF 3 -imidoyl structural units under mild reaction conditions, which has the advantages including broad substrates and good functional tolerance. In addition, a scale-up experiment and the synthetic transformations of the cycloadducts further highlight the synthetic utility. An enantio- and diastereoselective cyclopropanation of CF 3 -imidoyl sulfoxonium ylides with α,β-unsaturated 2-acyl imidazoles catalyzed by chiral-at-metal Rh(III) complex has been demonstrated for the first time. This work provides a practical approach for assembling 1,2,3-trisubstituted chiral cyclopropane with CF 3 -imidoyl structural units under mild reaction conditions, which has the advantages including broad substrates and good functional tolerance.

Green Synthesis and Catalysis
Shihezi University (CN), Karamay Central Hospital of Xinjiang (CN)
Openalex Percentile: Top 82%
Cyclopropane Reaction Mechanisms
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