MISC

2008年9月

Photoreactions of bicyclic aziridines with alkenes and alkynes: a novel synthetic methodology for 8-azabicyclo[3.2.1]octane derivatives

ORGANIC & BIOMOLECULAR CHEMISTRY
  • Keitaro Ishii
  • ,
  • Motohiro Kido
  • ,
  • Masahiro Noji
  • ,
  • Shigeo Sugiyama

6
17
開始ページ
3186
終了ページ
3195
記述言語
英語
掲載種別
DOI
10.1039/b805801f
出版者・発行元
ROYAL SOC CHEMISTRY

The photochemical C-C bond cleavage of bicyclic aziridines 7 and subsequent [3 + 2] cycloaddition with electron-deficient alkenes and alkynes afforded the novel head-to-head adducts selectively and efficiently. The adducts contain the naturally occurring 8-azabicyclo[3.2.1]octane skeleton (e g. tropane alkaloids). The aziridine 8 fused with a 6-membered ring also afforded the cycloadducts but in poor yields. The methylaziridine 9 reacted with an electron-deficient alkene, affording the head-to-tail adduct 23 in addition to head-to-head adducts 22a and 22b. The photoreactions of bicyclic aziridines with alkenes and alkynes indicate a similar behavior to that of aziridines with a linear chain.


リンク情報
DOI
https://doi.org/10.1039/b805801f
CiNii Articles
http://ci.nii.ac.jp/naid/80019821703
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/18698479
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000259038100023&DestApp=WOS_CPL
ID情報
  • DOI : 10.1039/b805801f
  • ISSN : 1477-0520
  • CiNii Articles ID : 80019821703
  • PubMed ID : 18698479
  • Web of Science ID : WOS:000259038100023

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