Preparation and synthetic application of a novel ketene silyl acetal of methyl trifluoropyruvate.
[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.
Takikawa
Go
G
Department of Applied Chemistry, Faculty of Engineering, Okayama University, Japan.
Katagiri
Toshimasa
T
Uneyama
Kenji
K
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*
D000080:Acetals; D000447:Aldehydes; D005030:Ethylenes; D007659:Ketones; D005461:Fluorine; D019289:Pyruvic Acid; C116609:3-hydroxybutanal; D008274:Magnesium; C008223:ketene