MISC

2017年12月

Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions

JOURNAL OF ORGANIC CHEMISTRY
  • Keita Takubo
  • ,
  • Ahmed A. B. Mohamed
  • ,
  • Takafumi Ide
  • ,
  • Kazuyuki Saito
  • ,
  • Takashi Ikawa
  • ,
  • Takehiko Yoshimitsu
  • ,
  • Shuji Akai

82
24
開始ページ
13141
終了ページ
13151
記述言語
英語
掲載種別
DOI
10.1021/acs.joc.7b02208
出版者・発行元
AMER CHEMICAL SOC

The dienone-phenol rearrangement is a useful tool for the synthesis of highly substituted phenols. In our previous study of the rearrangement of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienone under deoxyfluorination conditions, bond migration proceeded with very poor regioselectivity. In this paper, an acid-mediated rearrangement, of O-perfluoroalkylsulfonyl difluorides with regioselective migration toward the beta'-carbon is reported. This method allowed the synthesis of a fluorinated analog of allocolchicinoids with improved total yield. Successful application to other substrates was also demonstrated.


リンク情報
DOI
https://doi.org/10.1021/acs.joc.7b02208
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000418392600018&DestApp=WOS_CPL

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