Gold(I)-Catalyzed Tandem Cycloisomerization and Fluorination of 1,3(4)-Enyne Esters with NFSI: One-Pot Assembly of 5-Fluoro- Cyclopentenones

被引：20

作者：

Chen, Xianxiao ^{[1
]}

Zhou, Yuanyuan ^{[1
]}

Hong, Mei ^{[1
]}

Ling, Yuan ^{[1
]}

Yin, Dongliang ^{[1
]}

Wang, Shifa ^{[1
]}

Zhang, Xiaoxiang ^{[1
]}

Rao, Weidong ^{[1
]}

机构：

[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Key Lab Biomass Based Green Fuels & Chem, Nanjing 210037, Jiangsu, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 19期

基金：

中国国家自然科学基金;

关键词：

cycloisomerization; fluorination; 5-fluoro-cyclopentenones; gold; enyne esters; ALPHA-FLUOROKETONES; RAUTENSTRAUCH REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; GOLD CATALYSIS; DECARBOXYLATIVE FLUORINATION; N-FLUOROBENZENESULFONIMIDE; NUCLEOPHILIC FLUORINATION; BMS-204352 MAXIPOST(TM); DIAZOCARBONYL COMPOUNDS; MOLECULAR COMPLEXITY;

D O I：

10.1002/adsc.201800701

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient synthetic approach for the synthesis of 5-fluoro-cyclopentenones containing a fluorine-substituted carbon stereocenter that relies on gold(I)-catalyzed cycloisomerization and fluorination sequence of 1,3(4)-enyne esters with N-fluorbenzensulfonimide (NFSI) is described. This tandem transformation exhibited a broad substrate scope and excellent functional group compatibility, providing a novel protocol for rapid assembly 5-fluoro-cyclopentenones in good to excellent yields under mild reaction conditions. The mechanistic studies revealed that the transformation involves a gold-catalyzed cycloisomerization and electrophilic fluorination cascade to give the 5-fluoro-cyclopentenones.

引用

页码：3700 / 3708

页数：9

共 97 条

[91] Efficient synthesis of cyclopentenones from enynyl acetates via tandem Au(I)-catalyzed 3,3-rearrangement and the Nazarov reaction [J].