ID 58410
フルテキストURL
著者
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
抄録
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.
発行日
2018-10-22
出版物タイトル
Journal of the American Chemical Society
140巻
45号
出版者
American Chemical Society
開始ページ
15425
終了ページ
15429
ISSN
00027863
NCID
AA00692602
資料タイプ
学術雑誌論文
言語
English
OAI-PMH Set
岡山大学
論文のバージョン
Author
PubMed ID
DOI
Web of Science KeyUT
関連URL
isVersionOf https://doi.org/10.1021/jacs.8b09297
助成機関名
文部科学省
助成番号
26248030
18H03911
17K19122
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