Chiral and achiral lithium amides having a fluorous ponytail: Preparation and evaluation as a recycling reagent for lithium enolate generation

Hiroshi Matsubara*, Louis Maeda, Hiroyuki Sugiyama, Ilhyong Ryu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Diisopropylamine derivatives bearing a perfluoroalkyl chain were prepared and converted to the corresponding lithium amides by treatment with n-butyllithium. The fluorous lithium amides reacted with ketones to efficiently produce lithium enolates. Asymmetric deprotonation of prochiral ketones was also studied using lithium amides derived from chiral fluorous amines, which gave optical yields comparable with the parent nonfluorous chiral lithium amides. These reusable fluorous amines can be easily recovered by liquid-liquid extraction or chromatographic separation.

Original languageEnglish
Pages (from-to)2901-2912
Number of pages12
JournalSynthesis
Issue number18
DOIs
StatePublished - 17 Sep 2007

Keywords

  • Asymmetric deprotonation
  • Chiral amine
  • Enolate
  • Fluorous
  • LDA
  • Recycling

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