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

Research output: Contribution to journalArticle

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.
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Original languageEnglish
Pages (from-to)5182-5185
Number of pages4
JournalOrganic Letters
Volume19
Issue number19
Early online date8 Sep 2017
DOIs
StatePublished - 6 Oct 2017

    Research areas

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

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