Synthesis of Dioxo-Azabicyclo[3.2.1]octanes\nvia Hypervalent\nIodine-Mediated Domino Reaction

Bicyclo[3.2.1]octane (BCO) skeleton\nwidely exists in\nnatural products\nand biologically active molecules, whereas the development of convenient\napproaches to construct this structure remains a challenge. Herein,\nwe describe a cascade reaction to synthesize 6,8-dioxa-3-azabicycle[3.2.1]octane\nderivatives from β-keto allylamines via an oxidation–cyclization\nreaction. A series of dioxo-azabicyclo[3.2.1]octanes bearing a quaternary\ncarbon center were obtained in good yields under mild reaction conditions.\nMoreover, the mechanistic rationale for this novel domino reaction\nis supported by control experiments.

Publication Details

Journal
Figshare
Published
2024-10-16
DOI
https://doi.org/10.1021/acs.joc.4c02023.s001
Primary Topic
Advanced Synthetic Organic Chemistry
Type
article
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article

Synthesis of Dioxo-Azabicyclo[3.2.1]octanes\nvia Hypervalent\nIodine-Mediated Domino Reaction

Figshare
Advanced Synthetic Organic Chemistry
article

Synthesis of Dioxo-Azabicyclo[3.2.1]octanes\nvia Hypervalent\nIodine-Mediated Domino Reaction

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Abstract

Bicyclo[3.2.1]octane (BCO) skeleton\nwidely exists in\nnatural products\nand biologically active molecules, whereas the development of convenient\napproaches to construct this structure remains a challenge. Herein,\nwe describe a cascade reaction to synthesize 6,8-dioxa-3-azabicycle[3.2.1]octane\nderivatives from β-keto allylamines via an oxidation–cyclization\nreaction. A series of dioxo-azabicyclo[3.2.1]octanes bearing a quaternary\ncarbon center were obtained in good yields under mild reaction conditions.\nMoreover, the mechanistic rationale for this novel domino reaction\nis supported by control experiments.

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Openalex Percentile: Top 73%
Advanced Synthetic Organic Chemistry
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Synthesis of Dioxo-Azabicyclo[3.2.1]octanes\nvia Hypervalent\nIodine-Mediated Domino Reaction · Figshare (2024) | TGRS Research Map | TGRS