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

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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
JournalOrganic Letters
VolumeIn press
Early online date8 Sep 2017
StateE-pub ahead of print - 8 Sep 2017

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