Synthesis of Organofluorine Compounds Using the Ene Reaction of N-(p-Toluenesulfonyl)trifluoroacetaldehyde Imine

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概要

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• N-Tosyltrifluoroacetaldehyde imine (4) reacted with terminal olefins by only heating together to give the ene reactin products. This means the imine is much more reactive than trifluoroacetaldehyde (2) itself as an enophile. However, 4 was very sensitive to moisture and the yields were low even if it was used without isolation. Further, it did not react with non-terminal olefins. In the course on study of the mechanism of this reaction, we found that N-(2,2,2-trifluoro-1-ethoxyethyl)tosylamide (12), obtained by the reaction of trifluoroacetaldehyde ethyl hemiacetal (1) with tosylamide (3) in the presence of titanium(IV) chloride followed by addition of ethanol, reacted in the presence of sodium hydride and titanium(IV) chloride to give the same products from the ene reaction of 4 in much better yields. Interestingly, this reaction proceeded with non-terminal olefins.

• 公益社団法人日本薬学会の論文
• 1999-05-15

著者

• 安藤 章

  Faculty of Pharmaceutical Sciences, Setsunan University

• Ando A

  Faculty Of Pharmaceutical Sciences Setsunan University

• OMOTE Masaaki

  Faculty of Pharmaceutical Sciences

• ANDO Akira

  Faculty of Pharmaceutical Sciences

• KUMADAKI Itsumaro

  Faculty of Pharmaceutical Sciences

• JONOSHITA Shuichi

  Faculty of Pharmaceutical Sciences, Setsunan University

• HARADA Atsuhiro

  Faculty of Pharmaceutical Sciences, Setsunan University

• Omote M

  Faculty Of Pharmaceutical Sciences Setsunan University

• Kumadaki I

  Faculty Of Pharmaceutical Sciences Setsunan University

• Harada Atsuhiro

  Faculty Of Pharmaceutical Sciences Setsunan University

• Jonoshita S

  Setsunan Univ. Osaka Jpn

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