2017年12月
Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions
JOURNAL OF ORGANIC CHEMISTRY
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- 巻
- 82
- 号
- 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
- ID情報
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- DOI : 10.1021/acs.joc.7b02208
- ISSN : 0022-3263
- Web of Science ID : WOS:000418392600018