Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: synthesis of trihalomethylated spiro[indoline-3,2'-pyrrolidin]2-ones and spiro[indoline-3,3'-pyrrolizin]-2-ones

被引：33
|
作者：
Barkov, Alexey Yu. [1 ]
Zimnitskiy, Nikolay S. [1 ]
Korotaev, Vladislav Yu. [1 ]
Kutyashev, Igor B. [1 ]
Moshkin, Vladimir S. [1 ]
Sosnovskikh, Vyacheslav Ya. [1 ]
机构：
[1] Ural Fed Univ, Inst Nat Sci, Ekaterinburg 620000, Russia
来源：
TETRAHEDRON | 2016年 / 72卷 / 43期
基金：
俄罗斯科学基金会;
关键词：
3,3,3-Trihalogeno-1-nitropropenes; Stabilised azomethine ylides; 1,3-Dipolar cycloaddition; Spirooxindoles; ALPHA-AMINO-ACIDS; NATURAL-PRODUCTS; REGIOSELECTIVE SYNTHESIS; DECARBOXYLATIVE ROUTE; ORGANIC-SYNTHESIS; DERIVATIVES; 3,3,3-TRICHLORO(TRIFLUORO)-1-NITROPROPENES; 1,1,1-TRICHLORO-3-NITROPROPENE; 2-MORPHOLINOALK-1-ENES; SPIROOXINDOLES;
D O I：
10.1016/j.tet.2016.09.017
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reactions of 3,3,3-trihalogen-1-nitropropenes with N-alkyl-alpha-amino acids (sarcosine, proline) and isatins proceed regio- and diastereoselectively to give a wide range of trihalomethylated spiro[indoline-3,2'pyrrolidin]-2-ones and spiro[indoline-3,3'-pyrrolizin]-2-ones in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate stabilised azomethine ylide at the double bond of the nitroalkenes. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6825 / 6836
页数：12
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