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ID 58410
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Author
Sobi, Asako Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University ORCID Kaken ID publons researchmap
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 ORCID Kaken ID publons researchmap
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.
Published Date
2018-10-22
Publication Title
Journal of the American Chemical Society
Volume
volume140
Issue
issue45
Publisher
American Chemical Society
Start Page
15425
End Page
15429
ISSN
00027863
NCID
AA00692602
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
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Author
PubMed ID
DOI
Web of Science KeyUT
Related Url
isVersionOf https://doi.org/10.1021/jacs.8b09297
Funder Name
Ministry of Education, Culture, Sports, Science and Technology
助成番号
26248030
18H03911
17K19122