Gold-catalyzed intermolecular amination of allyl azides with ynamides:Efficient construction of 3-azabicyclo[3.1.0]scaffold  

作　　者：Chong-Yang Shi Jian-Xing Gong Zhen Li Chao Shu Long-Wu Ye Qing Sun Bo Zhou Xin-Qi Zhu 

机构地区：[1]College of Chemistry and Chemical Engineering,Yunnan Normal University,Kunming 650500,China [2]Key Laboratory of Chemical Biology of Fujian Province,State Key Laboratory of Physical Chemistry of Solid Surfaces,and College of Chemistry and Chemical Engineering,Xiamen University,Xiamen 361005,China [3]State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China [4]Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle,Nanchang Hangkong University,Nanchang 330063,China

出　　处：《Chinese Chemical Letters》2025年第2期356-360,共5页中国化学快报(英文版)

基　　金：financial support from the National Natural Science Foundation of China(Nos.22125108,22331004 and 22121001);Yunnan Normal University,Applied Basic Research Projects of Yunnan Province(No.202101AT070217);the Jiangxi Provincial Natural Science Foundation(No.20224BAB213013);the Jiangxi Provincial Department of Education in Science and Technology Program Project(No.GJJ210906)。

摘　　要：Gold-catalyzed amination reactions based on azides viaα-imino gold carbene intermediates have attracted extensive attention in the past decades because this methodology leads to the facile and efficient construction of synthetically useful N-containing molecules,especially valuable N-heterocycles.However,successful examples of intermolecular generation ofα-imino gold carbenes by using azides as amination reagents are rarely explored probably due to the weak nucleophilicity of azides.Herein,we disclose an efficient gold-catalyzed intermolecular aminative cyclopropanation of ynamides with the allyl azides,enabling flexible synthesis of a wide range of valuable 3-azabicyclo[3.1.0]hex-2-ene derivatives in good to excellent yields with excellent diastereoselectivities.Importantly,this protocol represents the first use of allyl azide as an efficient amination reagent in gold-catalyzed alkyne amination reactions.

关 键 词：GOLD AZIDES Alkynes AMINATION HETEROCYCLES 

分 类 号：O621.251[理学—有机化学]