Phosphine-Catalyzed Cascade Cycloaddition of Vinyl Oxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3<i>H</i>)-furanone Scaffolds

In this work, we developed a phosphine-catalyzed cascade lactonization/[2 + 1] annulation reaction between vinyl oxiranes and sulfonium compounds for the highly diastereoselective construction of spiro-2(3<i>H</i>)-furanone skeletons. The cascade cycloaddition proceeds via the 2(5<i>H</i>)-furanone phosphonium intermediate, introducing an oxygen-containing active intermediate for phosphine catalysis. These findings highlight the significant potential of harnessing vinyl oxiranes as versatile synthons for constructing spirocyclic compounds through simultaneous multicyclic skeleton formation.

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Publication Details

Journal
Organic Letters
Published
2025-01-09
DOI
https://doi.org/10.1021/acs.orglett.4c03633
Citations
3
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
2.81

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article

Phosphine-Catalyzed Cascade Cycloaddition of Vinyl Oxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3H)-furanone Scaffolds

Xin Zhao, Chung‐Ming Sun, Hongchao Guo, Chang Wang et al.
3 citations
Organic Letters
Catalytic C–H Functionalization Methods
2.81
article

Phosphine-Catalyzed Cascade Cycloaddition of Vinyl Oxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3H)-furanone Scaffolds

Xin Zhao, Chung‐Ming Sun, Hongchao Guo, Chang Wang, Haiyang Wang, Jiaxin Qu, Wei Du, Thomas P. Yang, Chia‐Yu Wu
article en
3 citations

Abstract

In this work, we developed a phosphine-catalyzed cascade lactonization/[2 + 1] annulation reaction between vinyl oxiranes and sulfonium compounds for the highly diastereoselective construction of spiro-2(3<i>H</i>)-furanone skeletons. The cascade cycloaddition proceeds via the 2(5<i>H</i>)-furanone phosphonium intermediate, introducing an oxygen-containing active intermediate for phosphine catalysis. These findings highlight the significant potential of harnessing vinyl oxiranes as versatile synthons for constructing spirocyclic compounds through simultaneous multicyclic skeleton formation.

Organic LettersVol. 27(3)
Shandong First Medical University (CN), China Agricultural University (CN)
Natural Science Foundation of Shandong Province, Shandong First Medical University
Openalex Percentile: Top 12%
Catalytic C–H Functionalization Methods
2.81
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