論文

査読有り
2008年12月

Efficient Formation of Ring Structures Utilizing Multisite Activation by Indium Catalysis

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  • Yoshimitsu Itoh
  • ,
  • Hayato Tsuji
  • ,
  • Ken-ichi Yamagata
  • ,
  • Kohei Endo
  • ,
  • Iku Tanaka
  • ,
  • Masaharu Nakamura
  • ,
  • Eiichi Nakamura

130
50
開始ページ
17161
終了ページ
17167
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1021/ja805657h
出版者・発行元
AMER CHEMICAL SOC

Lewis acidic indium(III) salts, in particular In(NTf(2))(3), effect the conversion of alpha-(omega'-alkynyl)-beta-ketoesters; and omega-alkynyl-beta-ketoesters to the corresponding cyclic products in a manner known as the Coniaene reaction. This reaction can lead to the creation of five- to fifteen-membered-ring carbocycles and heterocycles in good to excellent yields. The synthetic features of the reaction are a relatively low catalyst loading, as low as 0.01 mol % in the best case, as well as no requirement of solvent for five-membered-ring formation and the requirement of only moderately dilute reaction conditions for medium-sized-ring formation. The high reactivity of indium salts is due to the double activation of the beta-ketoester substrate containing an acetylene function. The indium metal activates the beta-ketoester moiety by the formation of an indium enolate, and this indium metal electrophilically activates the alkyne moiety. Such a strong push-pull activation of the substrate by a single metal circumvents the disadvantage of entropic and enthalpic factors generally associated with the formation of medium- and large-sized rings. The reaction allows the ready formation of a fifteen-membered-ring carbocycle, from which di-muscone has been synthesized.

リンク情報
DOI
https://doi.org/10.1021/ja805657h
J-GLOBAL
https://jglobal.jst.go.jp/detail?JGLOBAL_ID=200902284645215460
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000263320400059&DestApp=WOS_CPL
ID情報
  • DOI : 10.1021/ja805657h
  • ISSN : 0002-7863
  • J-Global ID : 200902284645215460
  • Web of Science ID : WOS:000263320400059

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