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

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 pro...

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Veröffentlicht in:	Organic letters 2010-11, Vol.12 (22), p.5104-5107
Hauptverfasser:	Kawai, Hiroyuki, Tachi, Kentaro, Tokunaga, Etsuko, Shiro, Motoo, Shibata, Norio
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkynes - chemistry Bromides - chemistry Catalysis Cinchona Alkaloids - chemistry Combinatorial Chemistry Techniques Ketones - chemistry Methanol - analogs & derivatives Methanol - chemical synthesis Methanol - chemistry Molecular Structure Propanols - chemistry Quaternary Ammonium Compounds - chemistry Stereoisomerism Trimethylsilyl Compounds - chemical synthesis Trimethylsilyl Compounds - chemistry
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Zusammenfassung:	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.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol102189c