2005•The Journal of Organic ChemistryRequires access

Preparation and Synthetic Application of a Novel Ketene Silyl Acetal of Methyl Trifluoropyruvate

Go Takikawa, Toshimasa Katagiri, Kenji Uneyama

Abstract

[reaction: see text] A novel trifluoromethyl ketene silyl acetal (4) of methyl trifluoropyruvate (1) was prepared in 82% yield by metal Mg reduction in a (TMS)Cl/THF system. Subsequent carbon-carbon bond formation such as Mukaiyama aldol, Michael addition, and other nucleophilic reactions of 4 at the trifluoromethylated carbon with various electrophiles gave various coupling products in high yields.

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Key concepts: Ketene, Acetal, Chemistry, Silylation, Organic chemistry, Catalysis