Gold-catalyzed Reactions of 3-Alkynyloxireno[2, 3-b]chromenones to Form 3(2H)-Furanones via a Domino Pathway

被引：10

作者：

Hu, Feng ^{[1
]}

Yan, Jianwei ^{[1
]}

Cheng, Ming ^{[1
]}

Hu, Youhong ^{[1
]}

机构：

[1] Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2013年 / 8卷 / 02期

基金：

中国国家自然科学基金;

关键词：

furanones; domino reactions; gold; nucleophilic addition; oxidation; HIGHLY SUBSTITUTED FURANS; 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE DDQ; EFFICIENT SYNTHESIS; TANDEM REACTION; KETONES; 3-(1-ALKYNYL)CHROMONES; CYCLOADDITION; CONSTRUCTION; DIVERSITY; 2-(1-ALKYNYL)-2-ALKEN-1-ONES;

D O I：

10.1002/asia.201200974

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

3(2H)-Furanones are efficiently generated from 3-alkynyl oxireno[2,3-b]chromenones by an Au/DDQ-catalyzed domino reaction through a pathway composed of cyclization, C?C cleavage, nucleophilic addition, oxidation, and nucleophilic addition. It was found that stoichiometric AuCl3 or catalytic Au with stoichiometric DDQ can oxidize the benzylic sp3 C?H bond to facilitate nucleophilic addition.

引用

页码：482 / 487

页数：6

共 45 条

[1] Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].