靛红衍生的亚胺叶立德与 2H-氮杂环丙烷的 1,3-偶极环加成反应：1,3-二氮杂螺[双环[3.1.0]己烷]氧吲哚的立体选择性合成。
1,3-Dipolar Cycloaddition of Isatin-Derived Azomethine Ylides with 2 H-Azirines: Stereoselective Synthesis of 1,3-Diazaspiro[bicyclo[3.1.0]hexane]oxindoles.
机构信息
AVIDIN Ltd. , Alsó kikötő sor 11/D, Szeged H-6726 , Hungary.
Department of Organic Chemistry , University of Szeged , Dóm tér 8, H-6720 Szeged , Hungary.
出版信息
J Org Chem. 2019 Apr 5;84(7):4273-4281. doi: 10.1021/acs.joc.9b00242. Epub 2019 Mar 19.
A regio- and diastereoselective 1,3-dipolar cycloaddition of 2 H-azirines with azomethine ylides generated in situ from isatins and α-amino acids has been elaborated, affording an unprecedented aziridine-fused spiro[imidazolidine-4,3'-oxindole] framework. This one-pot three-component reaction tolerates a wide range of substrates and enables the construction of highly diverse 1,3-diazaspiro[bicyclo[3.1.0]hexane]oxindoles in isolated yields up to 81% under mild conditions.
已详细阐述了 2H-氮丙啶与异吲哚啉和α-氨基酸原位生成的亚胺叶立德的区域和立体选择性 1,3-偶极环加成反应，得到了前所未有的氮丙啶稠合螺[咪唑烷-4,3'-氧吲哚]骨架。该一锅法三组分反应可耐受广泛的底物，并能在温和条件下以高达 81%的分离收率构建高度多样化的 1,3-二氮杂螺[双环[3.1.0]己烷]氧吲哚。
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