Palladium-Catalyzed Intermolecular Oxyvinylcyclization of Alkenes with Alkynes: An Approach to 3-Methylene γ-Lactones and Tetrahydrofurans

被引：52

作者：

Zhang, Zhenming ^{[1
]}

Ouyang, Lu ^{[1
]}

Wu, Wanqing ^{[1
]}

Li, Jianxiao ^{[1
]}

Zhang, Zhicai ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 22期

基金：

中国国家自然科学基金;

关键词：

STEREOSELECTIVE-SYNTHESIS; IONIC LIQUIDS; CARBOAMINATION REACTIONS; REGIOSELECTIVE SYNTHESIS; OXIDATIVE CYCLIZATION; HIGHLY REGIO; PRODUCT STEREOCHEMISTRY; INDOLE-DERIVATIVES; TERMINAL ALKYNES; C-C;

D O I：

10.1021/jo501606c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel chloropalladation-initiated intermolecular oxyvinylcyclization of alkenes with alkynoic acids or alkynols is developed. This protocol provides a series of 3-methylene γ-lactone and tetrahydrofuran derivatives in moderate to excellent yields with high stereoselectivities in the presence of PdCl2 and CuCl2 or CuCl2·2H2O. Besides a broad substrate scope, this method has the advantages of mild reaction conditions and easily accessible starting materials. Furthermore, the construction of C-Cl, C(sp2)-C(sp3), and C-O bonds in one step was also achieved in this transformation. © 2014 American Chemical Society.

引用

页码：10734 / 10742

页数：9

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