Asymmetric Synthesis of Chiral Cyclopropanes from Vinyl Sulfoxonium Ylides Catalyzed by a Chiral-at-Metal Rh(III) Complex

A chiral-at-metal Rh(III) complex-mediated [2+1] cyclization of vinyl sulfoxonium ylides with α,β-unsaturated 2,2-acylimidazoles has been demonstrated for the first time. This work provides a practical approach for assembling 1,2,3-trisubstituted chiral cyclopropane with alkyl structural units, which had advantages such as a wide range of substrates, good functional group tolerance, and mild reaction conditions. In addition, further amplification experiments and transformation of cycloaddition products were carried out to highlight the practicality of the method.

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Publication Details

Journal
Organic Letters
Published
2024-09-17
DOI
https://doi.org/10.1021/acs.orglett.4c03051
Citations
15
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
3.75

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article

Asymmetric Synthesis of Chiral Cyclopropanes from Vinyl Sulfoxonium Ylides Catalyzed by a Chiral-at-Metal Rh(III) Complex

Jun Wang, Xiaoting Xie, Shiwu Li, Zhifei Zhao
15 citations
Organic Letters
Cyclopropane Reaction Mechanisms
3.75
article

Asymmetric Synthesis of Chiral Cyclopropanes from Vinyl Sulfoxonium Ylides Catalyzed by a Chiral-at-Metal Rh(III) Complex

Jun Wang, Xiaoting Xie, Shiwu Li, Zhifei Zhao
article en
15 citations

Abstract

A chiral-at-metal Rh(III) complex-mediated [2+1] cyclization of vinyl sulfoxonium ylides with α,β-unsaturated 2,2-acylimidazoles has been demonstrated for the first time. This work provides a practical approach for assembling 1,2,3-trisubstituted chiral cyclopropane with alkyl structural units, which had advantages such as a wide range of substrates, good functional group tolerance, and mild reaction conditions. In addition, further amplification experiments and transformation of cycloaddition products were carried out to highlight the practicality of the method.

Organic LettersVol. 26(38)
Shihezi University (CN), Nanyang Institute of Technology (CN)
National Natural Science Foundation of China, Shihezi University, Key Scientific Research Project of Colleges and Universities in Henan Province
Openalex Percentile: Top 6%
Cyclopropane Reaction Mechanisms
3.75
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Asymmetric Synthesis of Chiral Cyclopropanes from Vinyl Sulfoxonium Ylides Catalyzed by a Chiral-at-Metal Rh(III) Complex — Jun Wang, Xiaoting Xie, et al. · Organic Letters (2024) | TGRS Research Map | TGRS