Electrochemical\nReductive Bimolecular Cycloaddition\nof 2‑Arylideneindane-1,3-diones for the Synthesis of Spirocyclopentanole\nIndane-1,3-diones

An electrochemical reductive bimolecular cycloaddition\nof 2-arylideneindane-1,3-diones\nhas been reported for the synthesis of spirocyclopentanole indane-1,3-diones\nbearing five contiguous stereocenters with vicinal tetrasubstituted\nstereocenters, especially involving a quaternary carbon center, in\nmoderate to good yields and excellent diastereoselectivities. The\npresent protocol features mild reaction conditions, no external chemical\nredox reagents, excellent atom economy, and gram-scale synthesis.\nIn addition, a mechanistic investigation indicates that the reactions\nproceed through a radical pathway.

Publication Details

Journal
Figshare
Published
2024-12-25
DOI
https://doi.org/10.1021/acs.joc.4c02481.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Electrochemical\nReductive Bimolecular Cycloaddition\nof 2‑Arylideneindane-1,3-diones for the Synthesis of Spirocyclopentanole\nIndane-1,3-diones

Figshare
Radical Photochemical Reactions
article

Electrochemical\nReductive Bimolecular Cycloaddition\nof 2‑Arylideneindane-1,3-diones for the Synthesis of Spirocyclopentanole\nIndane-1,3-diones

article en

Abstract

An electrochemical reductive bimolecular cycloaddition\nof 2-arylideneindane-1,3-diones\nhas been reported for the synthesis of spirocyclopentanole indane-1,3-diones\nbearing five contiguous stereocenters with vicinal tetrasubstituted\nstereocenters, especially involving a quaternary carbon center, in\nmoderate to good yields and excellent diastereoselectivities. The\npresent protocol features mild reaction conditions, no external chemical\nredox reagents, excellent atom economy, and gram-scale synthesis.\nIn addition, a mechanistic investigation indicates that the reactions\nproceed through a radical pathway.

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Radical Photochemical Reactions
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Electrochemical\nReductive Bimolecular Cycloaddition\nof 2‑Arylideneindane-1,3-diones for the Synthesis of Spirocyclopentanole\nIndane-1,3-diones · Figshare (2024) | TGRS Research Map | TGRS