通过 4-氨基吡唑啉酮、醛和吲哚啉的 1,3-偶极环加成反应，立体选择性合成基于吲哚啉的螺[吡唑啉酮-4,2'-吡咯烷]支架。
Diastereoselective synthesis of indolenine-based spiro[pyrazolone-4,2'-pyrrolidine] scaffolds via 1,3-dipolar cycloaddition of 4-aminopyrazolones, aldehydes, and indolenines.
机构信息
State Key Laboratory of Fine Chemicals, Department of Pharmaceutical Sciences, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, People's Republic of China.
出版信息
Org Biomol Chem. 2021 Aug 28;19(32):6964-6968. doi: 10.1039/d1ob01135a. Epub 2021 Aug 1.
In this work, we report a one-pot [3 + 2] cycloaddition of 4-aminopyrazolones, indolenines, and aldehydes. The reaction utilized in situ generated azomethine ylides as 1,3-dipoles and 2-alkenylindolenines as dipolarophiles affording indolenine-derived spiro[pyrazolone-4,2'-pyrrolidine] scaffolds with four contiguous stereocenters with excellent yields (up to 95%) and diastereoselectivities (up to >20 : 1 dr) under simple conditions. The in situ generation of azomethine ylides and dipolarophiles in one pot is a unique feature of this process.
在这项工作中，我们报告了一种一锅[3 + 2]环加成反应，涉及 4-氨基吡唑啉酮、吲哚啉和醛。该反应利用原位生成的亚胺叶立德作为 1,3-偶极子，2-烯基吲哚啉作为偶极子，以优异的收率（高达 95%）和非对映选择性（高达>20:1 dr）提供了吲哚啉衍生的螺[吡唑啉-4,2'-吡咯烷]支架，具有四个连续的立体中心。亚胺叶立德和偶极子的原位生成是该反应的一个独特特点。
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