New derivatives of trifluoroacetyl acetaldehyde and trifluoroaldol

Ivan S. Kondratov, Igor I. Gerus, Aleksey D. Kacharov, Marina G. Gorbunova, Valery P. Kukhar, Roland Fröhlich

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

The reaction of β-ethoxyvinyl trifluoromethyl ketone 1 with O-nucleophiles such as alcohols and diols leads to various derivatives of trifluoroacetyl acetaldehyde, such as β-alkoxyvinyl trifluoromethyl ketones 3 and cyclic keto acetals 4. Several derivatives synthesized contain chiral auxiliaries. Reduction of the compounds 1, 3, 4 under various reaction conditions leads to the trifluoroaldol derivatives 6, 7, 9, 10 containing a protected aldehyde group. The compounds obtained are useful building blocks in fluoroorganic synthesis.

Original languageEnglish (US)
Pages (from-to)355-362
Number of pages8
JournalJournal of Fluorine Chemistry
Volume126
Issue number3
DOIs
StatePublished - Mar 2005
Externally publishedYes

Keywords

  • Chiral auxiliary
  • Fluorinated β-alkoxyvinyl ketones
  • Fluorinated β-keto acetals
  • O-nucleophiles
  • Reduction

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