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

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.

本文报道了一种可获得优异收率的γ,δ-不饱和α-氮代醛（γ,δ-unsaturated α-nitrogenated aldehydes）合成新方法。该方法以β-碘代烯酰胺衍生物（β-iodoenamide derivatives）与烯丙醇（allylic alcohols）为底物，通过铜偶联反应生成β-烯丙氧基烯酰胺衍生物（β-allyloxyenamide derivatives）。该中间体经加热后发生克莱森重排（Claisen rearrangement），最终得到γ,δ-不饱和α-氮代醛。