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Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane

  作者 KAWAI HIROYUKI; TACHI KENTARO; TOKUNAGA ETSUKO; SHIRO MOTOO; SHIBATA NORIO  
  选自 期刊  Organic Letters;  卷期  2010年12-22;  页码  5104-5107  
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[摘要]The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me4NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.

 
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