Enantioselective synthesis of β-fluoro-β-aryl-α-amino pentenamides by organocatalytic [2,3]-sigmatropic rearrangement

Kevin Kasten, Alexandra M. Z. Slawin, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)
1 Downloads (Pure)

Abstract

The tetramisole-promoted catalytic enantioselective [2,3]-sigmatropic rearrangement of quaternary ammonium salts bearing a (Z)-3-fluoro-3-arylprop-2-ene group generates, after addition of benzylamine, a range of β-fluoro-β-aryl-α-aminopentenamides containing a stereogenic tertiary fluorine substituent. Cyclic and acyclic nitrogen substituents as well as various aromatic substituents are tolerated, giving the β-fluoro-β-aryl-α-aminopentenamide products in up to 76% yield, 96:4 dr, and 98:2 er.
Original languageEnglish
Pages (from-to)5182-5185
Number of pages4
JournalOrganic Letters
Volume19
Issue number19
Early online date8 Sept 2017
DOIs
Publication statusPublished - 6 Oct 2017

Keywords

  • Flluorinated amino-acids
  • Allylic ammonium ylides
  • Kinetic resolution
  • Medicinal chemistry
  • Protein design
  • Catalysts
  • Mannich
  • Benzotetramisole
  • Straightforward
  • Cycloaddition

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