首页|Sequence[2,3]-Sigmatropic Rearrangement:One-Pot Synthesis of Propargyl Allenylamines

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

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Allenes,served as highly sought-after building blocks,are an indispensable component of synthetic chemistry.Their utility in modu-lating the chemical,physical,and pharmaceutical properties of organic compounds make allenes a desirable choice in various applica-tions.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 con-verted into propargyl ammonium salts,followed by a base-promoted[2,3]-sigmatropic rearrangement.This one-pot,two-step reac-tion proceeds in the absence of transition metals,displays a very broad scope,and does not require the introduction of the elec-tron-withdrawing group into the starting materials.

AllenePropargylamineC-N activationSigmatropic rearrangementMetal-freeSynthetic methodsDomino reactions

Huihui Feng、Yujuan Xie、Liliang Huang、Yongqing Xu、Junhai Huang、Huangdi Feng

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College of Chemistry and Chemical Engineering,Shanghai University of Engineering Science,Shanghai 201620,China

Shanghai Frontiers Science Research Center for Druggability of Cardiovascular noncoding RNA,Institute for Frontier Medical Technology,Shanghai University of Engineering Science,Shanghai 201620,China

2024

中国化学(英文版)
中国化学会 上海有机化学研究所

中国化学(英文版)

CSTPCD
影响因子:0.848
ISSN:1001-604X
年,卷(期):2024.42(18)