DMAP Catalyzed\nRing-Opening/Cycloaddition of Vinyl\nOxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane\nSkeletons

The present work develops a DMAP-catalyzed [3 + 2] cycloaddition\nof vinyl oxiranes with activated ketone compounds, affording dioxolane\nderivatives with moderate to excellent yields. This approach represents\nthe first Lewis base (LB)-catalyzed ring-opening reaction of vinyl\nepoxides, simultaneously providing a rare oxygen-containing active\nintermediate in this field. The gram-scale preparation and facile\nderivatization of the cycloadduct highlight the significant synthetic\npotential of this strategy.

Publication Details

Journal
Figshare
Published
2024-10-24
DOI
https://doi.org/10.1021/acs.orglett.4c03502.s001
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

DMAP Catalyzed\nRing-Opening/Cycloaddition of Vinyl\nOxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane\nSkeletons

Figshare
Synthesis and Catalytic Reactions
article

DMAP Catalyzed\nRing-Opening/Cycloaddition of Vinyl\nOxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane\nSkeletons

article en

Abstract

The present work develops a DMAP-catalyzed [3 + 2] cycloaddition\nof vinyl oxiranes with activated ketone compounds, affording dioxolane\nderivatives with moderate to excellent yields. This approach represents\nthe first Lewis base (LB)-catalyzed ring-opening reaction of vinyl\nepoxides, simultaneously providing a rare oxygen-containing active\nintermediate in this field. The gram-scale preparation and facile\nderivatization of the cycloadduct highlight the significant synthetic\npotential of this strategy.

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Synthesis and Catalytic Reactions
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