Construction of Nitrogen-Containing Three-Dimensional Frameworks via Formation and Cycloaddition of <i>endo</i>-Cyclic Azomethine Ylide

Triggered by the reaction of an oxime ether with a rhodium carbenoid, nitrogen-containing three-dimensional frameworks were constructed from linear motifs via the intramolecular cycloaddition of <i>endo</i>-cyclic azomethine ylide. In this transformation, successive stereocenters containing quaternary carbons were formed, affording the corresponding tricyclic compounds in moderate-to-good yields. The utility of these products was demonstrated through several transformations.

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Publication Details

Journal
Organic Letters
Published
2025-05-08
DOI
https://doi.org/10.1021/acs.orglett.5c01153
Citations
4
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
3.74

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article

Construction of Nitrogen-Containing Three-Dimensional Frameworks via Formation and Cycloaddition of endo-Cyclic Azomethine Ylide

Keizo Furuhashi, Yoe Matsuyuki, Satoshi Yokoshima, Nariyoshi Umekubo
4 citations
Organic Letters
Cyclopropane Reaction Mechanisms
3.74
article

Construction of Nitrogen-Containing Three-Dimensional Frameworks via Formation and Cycloaddition of endo-Cyclic Azomethine Ylide

Keizo Furuhashi, Yoe Matsuyuki, Satoshi Yokoshima, Nariyoshi Umekubo
article en
4 citations

Abstract

Triggered by the reaction of an oxime ether with a rhodium carbenoid, nitrogen-containing three-dimensional frameworks were constructed from linear motifs via the intramolecular cycloaddition of <i>endo</i>-cyclic azomethine ylide. In this transformation, successive stereocenters containing quaternary carbons were formed, affording the corresponding tricyclic compounds in moderate-to-good yields. The utility of these products was demonstrated through several transformations.

Organic LettersVol. 27(19)
Nagoya University (JP), Kumamoto University (JP)
Japan Agency for Medical Research and Development, Ministry of Education, Culture, Sports, Science and Technology, Japan Society for the Promotion of Science
Openalex Percentile: Top 8%
Cyclopropane Reaction Mechanisms
3.74
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