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

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

Publication Details

Journal
Figshare
Published
2025-01-09
DOI
https://doi.org/10.1021/acs.orglett.4c03633.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Phosphine-Catalyzed\nCascade Cycloaddition of Vinyl\nOxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3H)‑furanone Scaffolds

Figshare
Catalytic C–H Functionalization Methods
article

Phosphine-Catalyzed\nCascade Cycloaddition of Vinyl\nOxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3H)‑furanone Scaffolds

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Abstract

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

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Catalytic C–H Functionalization Methods
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Phosphine-Catalyzed\nCascade Cycloaddition of Vinyl\nOxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3<i>H</i>)‑furanone Scaffolds · Figshare (2025) | TGRS Research Map | TGRS