1-硫氰酸根合丁二烯的催化不对称狄尔斯-阿尔德反应/[3,3] 迁移重排串联反应
Catalytic Asymmetric Diels-Alder Reaction/[3,3] Sigmatropic Rearrangement Cascade of 1-Thiocyanatobutadienes.
作者信息
Zhou Yuhang, Lin Lili, Liu Xiaohua, Hu Xinyue, Lu Yan, Zhang Xiying, Feng Xiaoming
机构信息
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China.
出版信息
Angew Chem Int Ed Engl. 2018 Jul 16;57(29):9113-9116. doi: 10.1002/anie.201804811. Epub 2018 Jun 19.
A highly efficient asymmetric Diels-Alder/[3,3] sigmatropic rearrangement reaction of methyleneindolinones with 1-thiocyanatobutadienes has been realized by using a chiral N,N'-dioxide/nickel(II) complex as the catalyst. A range of cyclohexenyl isothiocyanates were synthesized in high yields with excellent diastereo- and enantioselectivities. Based on mechanistic studies, a catalytic cycle with possible transition-state models were proposed to explain the process.
通过使用手性N,N'-二氧化物/镍（II）配合物作为催化剂，实现了亚甲基吲哚酮与1-硫氰酸丁二烯的高效不对称狄尔斯-阿尔德/[3,3] 西格玛重排反应。以高收率合成了一系列环己烯基异硫氰酸酯，具有优异的非对映选择性和对映选择性。基于机理研究，提出了一个带有可能过渡态模型的催化循环来解释该过程。
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