Synthesis of γ,δ-Unsaturated α-Aminoaldehydes Using a Copper-Catalyzed Vinylation Reaction Followed by a Claisen Rearrangement

J Org Chem. 2016 Jun 17;81(12):5066-73. doi: 10.1021/acs.joc.6b00512. Epub 2016 Jun 1.


A new method to synthesize γ,δ-unsaturated α-nitrogenated aldehydes in very good yields is described herein. This method involves a copper-coupling reaction between β-iodoenamide derivatives and allylic alcohols to generate β-allyloxyenamide derivatives. The latter, when heated, undergo a Claisen rearrangement and form γ,δ-unsaturated α-nitrogenated aldehydes.

Publication types

  • Research Support, Non-U.S. Gov't