Direct Catalytic Asymmetric Aldol Reaction of α-Alkoxyamides to α-Fluorinated Ketones

Roman Pluta, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

α-Oxygen-functionalized amides found particular utility as enolate surrogates for direct aldol couplings with α-fluorinated ketones in a catalytic manner. Because of the likely involvement of open transition states, both syn- and anti-aldol adducts can be accessed with high enantioselectivity by judicious choice of the chiral ligands. A broad variety of alkoxy substituents on the amides and aryl and fluoroalkyl groups on the ketone were tolerated, and the corresponding substrates delivered a range of enantioenriched fluorinated 1,2-dihydroxycarboxylic acid derivatives with divergent diastereoselectivity depending on the ligand used. The amide moiety of the aldol adduct was transformed into a variety of functional groups without protection of the tertiary alcohol, showcasing the synthetic utility of the present asymmetric aldol process.

Original languageEnglish
Pages (from-to)2459-2463
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number8
DOIs
Publication statusPublished - 2019 Feb 18
Externally publishedYes

Keywords

  • 7-azaindolines
  • C−C bond formation
  • aldol reaction
  • asymmetric catalysis
  • fluorine

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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