Sequence [2,3]-Sigmatropic Rearrangement: One-Pot Synthesis of Proparggyl Allenylamines  

作　　者：Huihui Feng Yujuan Xie Lliang Huang Yongqing Xu Junhai Huang Huangdi Feng 

机构地区：[1]College of Chemistry and Chemical Engineering,Shanghai University of Engineering Science,Shanghai 201620,China [2]Shanghai Frontiers Science Research Centerfor Druggability of Cardiovascular noncoding RNA,Institute for Frontier Medical Technology Shanghai Universityof Engineering Science,Shanghai 201620,China

出　　处：《Chinese Journal of Chemistry》2024年第18期2223-2227,共5页中国化学（英文版）

基　　金：the National Natural Science Foundation of China(No.22078192);National Key Research and Development Program of China(Nos.2023YFC2412400,2023YFC2412403)forfinancial support.

摘　　要：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.

关 键 词：ALLENE PROPARGYLAMINE C-N activation Sigmatropic rearrangement METAL-FREE Synthetic methods Domino reactions 

分 类 号：O62[理学—有机化学]