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Mizoguchi, Haruki Graduate School of Environmental, Life, Natural Science and Technology, Okayama University ORCID Kaken ID researchmap
Obata, Takumi Graduate School of Environmental, Life, Natural Science and Technology, Okayama University
Hirai, Taiki Graduate School of Environmental, Life, Natural Science and Technology, Okayama University
Komatsu, Manaka Graduate School of Environmental, Life, Natural Science and Technology, Okayama University
Sakakura, Akira Graduate School of Environmental, Life, Natural Science and Technology, Okayama University ORCID Kaken ID publons researchmap
Abstract
Fleeting molecules possessing strained multiple bonds are important components in organic synthesis due to their ability to undergo various chemical reactions driven by the release of strain energy. Although the use of strained π-bonds as 2π components, represented by dienophiles in Diels–Alder reactions, has been well studied, “the strained diene (4π component) approach” for molecular construction remains underexplored. Herein, we report the design of a vinyl cyclic allene (1-vinyl-1,2-cyclohexadiene) as a highly reactive strained diene and the development of its Diels–Alder reactions. Experimental and computational studies of vinyl cyclic allenes revealed that this diene system undergoes cycloaddition with dienophiles regio- and stereoselectively under mild reaction conditions. These studies also provide insight into the reactivity and selectivity of the system. The strained diene approach enables the convergent construction of polycyclic molecules through bond disconnections distinct from conventional retrosynthetic analysis, thus offering an efficient strategy for the assembly of functional molecules.
Keywords
Activation strain model
Carbocycles
Diels–Alder reaction
Strained diene
Vinylated cyclic allene
Published Date
2025-06-26
Publication Title
Angewandte Chemie International Edition
Publisher
Wiley
Start Page
e202510319
ISSN
1433-7851
NCID
AA0052535X
Content Type
Journal Article
language
English
OAI-PMH Set
岡山大学
Copyright Holders
©2025 The Author(s).
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DOI
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Related Url
isVersionOf https://doi.org/10.1002/anie.202510319
License
http://creativecommons.org/licenses/by/4.0/
Citation
H. Mizoguchi, T. Obata, T. Hirai, M. Komatsu, A. Sakakura, Angew. Chem. Int. Ed. 2025, e202510319. https://doi.org/10.1002/anie.202510319
助成情報
23K04734: 1,2-メタレート転位の立体制御を基盤とするホウ素アート錯体のカップリング反応の開発 ( 独立行政法人日本学術振興会 / Japan Society for the Promotion of Science )
( 公益財団法人ウエスコ学術振興財団 / Wesco Scientific Promotion Foundation )
( 公益財団法人住友財団 / Sumitomo Foundation )