Reactions of novel trifluoromethyl propargylic carbocation with carbon nucleophiles |
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Authors: | Sung Lan Jeon Jang Bae Son In Howa Jeong |
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Institution: | a Department of Chemistry, Yonsei University, Wonju, Republic of Korea b Korea Research Institute of Chemical Technology, Daejeon, Republic of Korea |
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Abstract: | Trifluoromethyl propargylic carbocation I] generated from the reaction of 1-amino substituted 3-trifluoromethyl-2-propynyl trimethylsilyl ether 1 with TMSOTf in CH2Cl2 at −15 °C, followed by warming to room temperature reacted with 1.2 equiv of substituted benzenes, RMgBr and allylsilane to give the enones 3a-l and 5, respectively. The reaction of I] with anisole, followed by treatment with Grignard reagents afforded the corresponding allyl amine derivatives 7, which underwent cyclization reaction to give indene derivatives 8 by using 2 equiv of TMSOTf. |
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Keywords: | 3-Trifluoromethyl-2-propynyl trimethylsilyl ether Trifluoromethyl propargylic carbocation Carbon nucleophiles Trifluoromethylated enones Trifluoromethylated indenes |
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