Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative C-C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides

被引：124

作者：

Wang, Junwei ^{[1
]}

Yuan, Yucheng ^{[1
]}

Xiong, Rui ^{[1
]}

Zhang-Negrerie, Daisy ^{[1
]}

Du, Yunfei ^{[1
]}

Zhao, Kang ^{[1
]}

机构：

[1] Tianjin Univ, Tianjin Key Lab Modern Drug Delivery & High Effic, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 09期

基金：

中国国家自然科学基金;

关键词：

POLYVALENT IODINE COMPOUNDS; CATALYTIC ASYMMETRIC-SYNTHESIS; BIARYL COUPLING REACTION; ONE-POT SYNTHESIS; INTRAMOLECULAR CYCLIZATION; ENANTIOSELECTIVE SYNTHESIS; ALPHA-ARYLATION; DERIVATIVES; OXINDOLES; PIFA;

D O I：

10.1021/ol300418h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO2Et) In CF3CH2OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1' (E = CON(R-4)Ar) afforded the C-2-symmetric or unsymmetric spirooxindoles 3. These processes feature a metal-free oxidative C(sp(2))-C(sp(3)) bond formation, followed by oxidative hydroxylation or spirocyclization.

引用

页码：2210 / 2213

页数：4

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