Sequence [2,3]‐Sigmatropic Rearrangement: <scp>One‐Pot</scp> Synthesis of Propargyl Allenylamines
Huihui Feng, Huihui Feng, Yujuan Xie, Liliang Huang, Yongqing Xu, Junhai Huang, Huangdi Feng, Huangdi Feng
Abstract
Comprehensive Summary 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.