gem-Difluorination of Aminoalkynes via Highly Reactive Dicationic Species in Superacid HF-SbF5: Application to the Efficient Synthesis of Difluorinated Cinchona Alkaloid Derivatives
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- 作者：Anne-Cé ; line Cantet ; Hé ; lè ; ne Carreyre ; Jean-Pierre Gesson ; Marie-Paule Jouannetaud ; Brigitte Renoux
- 刊名：Journal of Organic Chemistry
- 出版年：2008
- 出版时间：April 4, 2008
- 年：2008
- 卷：73
- 期：7
- 页码：2875 - 2878
- 全文大小：115K
- 年卷期：v.73,no.7(April 4, 2008)
- ISSN：1520-6904
文摘
A variety of alkynylated amines, amides, and imides arereacted in the superacid system HF-SbF5 to give regioselectively new 
le">-gem-difluoroamines. The reaction, which isnot observed in pure HF, is consistent with the formation ofa dicationic intermediate (i.e., both vinylic and adjacentprotonated N-ammonium cations). Application to the regioselective and efficient synthesis of difluorinated cinchonaalkaloid derivatives is described.
le">-gem-difluoroamines. The reaction, which isnot observed in pure HF, is consistent with the formation ofa dicationic intermediate (i.e., both vinylic and adjacentprotonated N-ammonium cations). Application to the regioselective and efficient synthesis of difluorinated cinchonaalkaloid derivatives is described.