title: Preparation and synthetic application of a novel ketene silyl acetal of methyl trifluoropyruvate.
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.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Okayama University, Japan.
authors.forename: Go
authors.initials: G
authors.lastname: Takikawa
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Katagiri
authors.forename: Kenji
authors.initials: K
authors.lastname: Uneyama
mesh_terms: D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D005030:Ethylenes / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D019289:Pyruvic Acid / Q000737:chemistry*
chemical_list: D000080:Acetals; D000447:Aldehydes; D005030:Ethylenes; D007659:Ketones; D005461:Fluorine; D019289:Pyruvic Acid; C116609:3-hydroxybutanal; D008274:Magnesium; C008223:ketene