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

页码：6825 / 6836

页数：12

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