Sequence [2, 3]-Sigmatropic Rearrangement: One-Pot Synthesis of Propargyl Allenylamines
Huihui Feng , Yujuan Xie , Liliang Huang , Yongqing Xu , Junhai Huang , Huangdi Feng
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (18) : 2223 -2227.
Sequence [2, 3]-Sigmatropic Rearrangement: One-Pot Synthesis of Propargyl Allenylamines
Allenes, served as highly sought-after building blocks, are an indispensable component of synthetic chemistry. Their utility in modulating the chemical, physical, and pharmaceutical properties of organic compounds make allenes a desirable choice in various applications. Here, we report a facile method for the atom-economical synthesis of propargyl allenylamines via an underdeveloped [2, 3]-sigmatropic rearrangement. Our strategy employs easily accessible propargylamines as starting materials, which are first converted into propargyl ammonium salts, followed by a base-promoted [2, 3]-sigmatropic rearrangement. This one-pot, two-step reaction proceeds in the absence of transition metals, displays a very broad scope, and does not require the introduction of the electron-withdrawing group into the starting materials.
Allene / Propargylamine / C—N activation / Sigmatropic rearrangement / Metal-free / Synthetic methods / Domino reactions
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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