A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles

被引：18

作者：

Sun, Yin-Wei ^{[1
,2
]}

Tang, Xiang-Ying ^{[3
]}

Shi, Min ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 73期

基金：

中国国家自然科学基金;

关键词：

FURAN-YNE; PROPARGYLIC ESTERS; CYCLOADDITIONS; METATHESIS; ALKYNES; CYCLOISOMERIZATION; CYCLIZATION; ACCESS; MIGRATION; INDOLES;

D O I：

10.1039/c5cc05808b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of medium-sized heterocycles possessing a trans double bond is still a challenge. Herein, gold(I)-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade reaction of furans has been developed, providing highly efficient access to ten-and eleven-membered heterocycles with a broad substrate scope under mild reaction conditions. The reaction outcome features high chemo-selectivity at the C5-position of furan. Moreover, a trans-double bond was embodied in the medium ring system.

引用

页码：13937 / 13940

页数：4

共 13 条

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Chen, Ming
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CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (03) : 1009 - 1013
[12] One-Pot Synthesis of 4-Heteroaryl-Substituted Pyrazoles: A Gold-Catalyzed Oxidation/1,2-Heteroaryl Migration Cascade Constitutes the Key Step
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[13] Rapid construction of complex tetracyclic frameworks via a gold(I)-catalyzed tandem 1,2-acyloxy migration/[3+2] cycloaddition/Friedel-Crafts type cyclization reaction of linear enynyl esters
Sun, Haiyu
Xu, Shiyan
Xing, Zhimin
Liu, Lin
Feng, Shangbiao
Fang, Bowen
Xie, Xingang
She, Xuegong
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11): : 2109 - 2113

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