ID | 58410 |
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Author |
Sobi, Asako
Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University
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Kobashi, Takaaki
Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University
Takai, Kazuhiko
Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University
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Abstract | Cyclopropanation of alkenes is a well-established textbook reaction for the synthesis of cyclopropanes, where a “high-energy” carbene species is exploited to drive the reaction forward. However, little attention has been focused toward molecular transformations involving the reverse reaction, retro-cyclopropanation (RC). This is because of difficulties associated with both cleaving the two geminal C–C single bonds and exploiting the generated carbenes for further transformations in an efficient and selective manner. Here, we report that a molybdenum-based catalytic system overcomes the above challenges and effects the RC of cyclopropanes bearing a pyridyl group with the release of ethylene (alkene) and the subsequent intramolecular cyclization leading to pyrido[2,1-a]isoindoles. The reaction allows for the uncommon use of cyclopropanes as C1 synthetic units in contrast to most conventional reactions in which cyclopropanes are used as C3 synthetic units. We anticipate that this new strategy will pave the way for C1 cyclopropane chemistry.
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Published Date | 2018-10-22
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Publication Title |
Journal of the American Chemical Society
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Volume | volume140
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Issue | issue45
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Publisher | American Chemical Society
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Start Page | 15425
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End Page | 15429
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ISSN | 00027863
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NCID | AA00692602
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Content Type |
Journal Article
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language |
English
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OAI-PMH Set |
岡山大学
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File Version | author
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Related Url | isVersionOf https://doi.org/10.1021/jacs.8b09297
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Funder Name |
Ministry of Education, Culture, Sports, Science and Technology
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助成番号 | 26248030
18H03911
17K19122
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