Iodo-Carbocyclization of Electron-Deficient Alkenes: Synthesis of Oxindoles and Spirooxindoles

被引：106

作者：

Wei, Hai-Long ^{[1
]}

Piou, Tiffany ^{[1
]}

Dufour, Jeremy ^{[1
]}

Neuville, Luc ^{[1
]}

Zhu, Jieping ^{[1
,2
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

[2] Ecole Polytech Fed Lausanne, EPFL SB ISIC LSPN, Inst Chem Sci & Engn, CH-1015 Lausanne, Switzerland

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 09期

关键词：

H ACTIVATION REACTIONS; INDUCED POLYENE CYCLIZATIONS; CATALYZED DIRECT ARYLATION; ENANTIOSELECTIVE HALOCYCLIZATION; ORGANIC-SYNTHESIS; MOLECULAR-IODINE; NATURAL-PRODUCTS; ANION CAPTURE; FUNCTIONALIZATION; DERIVATIVES;

D O I：

10.1021/ol2005243

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclisative carbo-iodination of N-alkyl-N-arylacrylamide derivatives (3) in the presence of PhI(OAc)(2)/I-2 afforded functionalized 3-(iodomethyl)-3-substituted-indolin-2-ones (4) in good to excellent yields. With a suitably functionalized linear amide, spirooxindole 8 was prepared in a one-pot fashion via a sequence of iodo-arylation followed by an in situ base-promoted intramolecular S(N)2 reaction.

引用

页码：2244 / 2247

页数：4

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