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Substrate-Controlled Regioselectivity Switch in a Three-Component 1,3-Dipolar Cycloaddition Reaction to Access 3,3′-Pyrrolidinyl-Spirooxindoles Derivatives
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2022-05-11 , DOI: 10.1002/adsc.202200269
Kai‐Kai Wang 1, 2 , Yan‐Li Li 3 , Rong‐Xiang Chen 1 , Ai‐Li Sun 2 , Zhan‐Yong Wang 1 , Ying‐Chao Zhao 1 , Ming‐Yue Wang 1 , Shi Sheng 1
Affiliation  

The additive-free 1,3-dipolar cycloaddition reaction of isatin-derived azomethine ylides with α-cyano-α,β-unsaturated compounds was developed, which enabled diversity-oriented synthesis of a series of novel and structurally complex 3,3′-pyrrolidinyl-spirooxindoles derivatives containing four contiguous and two quaternary stereogenic centers in high yields (up to 92%) and excellent diastereoselectivities (up to >25:1 dr). The reaction displays switchable regioselectivity depending on the steric effect of the substrates.

中文翻译:

三组分 1,3-偶极环加成反应中底物控制的区域选择性开关以获得 3,3'-吡咯烷基-螺氧吲哚衍生物

开发了靛红衍生的偶氮甲碱叶立德与 α-氰基-α,β-不饱和化合物的无添加剂 1,3-偶极环加成反应,能够以多样性为导向合成一系列结构复杂的新型 3,3'-吡咯烷基-螺氧吲哚衍生物含有四个连续的和两个四元立体中心,产率高(高达 92%)和出色的非对映选择性(高达 >25:1 dr)。该反应根据底物的空间效应显示出可切换的区域选择性。
更新日期:2022-05-11
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